U.S. patent application number 14/647236 was filed with the patent office on 2015-11-05 for substituted [1,2,4] triazole compounds.
The applicant listed for this patent is BASF SE. Invention is credited to Nadege BOUDET, Ian Robert CRAIG, Jochen DIETZ, Ana ESCRIBANO CUESTA, Wassilios GRAMMENOS, Thomas GROTE, Egon HADEN, Erica May Wilson LAUTERWASSER, Jan Klaas LOHMANN, Bernd MUELLER.
Application Number | 20150313229 14/647236 |
Document ID | / |
Family ID | 50827208 |
Filed Date | 2015-11-05 |
United States Patent
Application |
20150313229 |
Kind Code |
A1 |
GRAMMENOS; Wassilios ; et
al. |
November 5, 2015 |
Substituted [1,2,4] Triazole Compounds
Abstract
The present invention relates to substituted [1,2,4]triazol
compounds of the formula I ##STR00001## wherein the substituents
are defined in the claims and the description, and the N-oxides and
the salts thereof for combating phytopathogenic fungi, and to the
use and methods for combating phytopathogenic fungi and to seeds
coated with at least one such compound. The invention also relates
to processes for preparing these compounds, intermediates,
processes for preparing such intermediates, and to compositions
comprising at least one compound I.
Inventors: |
GRAMMENOS; Wassilios;
(Ludwigshafen, DE) ; CRAIG; Ian Robert;
(Ludwigshafen, DE) ; BOUDET; Nadege; (Hemsbach,
DE) ; MUELLER; Bernd; (Frankenthal, DE) ;
DIETZ; Jochen; (Karlsruhe, DE) ; LAUTERWASSER; Erica
May Wilson; (Wachenheim, DE) ; LOHMANN; Jan
Klaas; (Lambsheim, DE) ; GROTE; Thomas;
(Wachenheim, DE) ; HADEN; Egon; (Speyer, DE)
; ESCRIBANO CUESTA; Ana; (Mannheim, DE) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
BASF SE |
Ludwigshafen |
|
DE |
|
|
Family ID: |
50827208 |
Appl. No.: |
14/647236 |
Filed: |
November 18, 2013 |
PCT Filed: |
November 18, 2013 |
PCT NO: |
PCT/EP2013/074009 |
371 Date: |
May 26, 2015 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
61730091 |
Nov 27, 2012 |
|
|
|
Current U.S.
Class: |
504/100 ;
514/383; 548/267.4; 548/268.6; 549/551; 549/553; 549/554; 549/561;
558/424; 560/62; 562/472; 564/171; 568/637 |
Current CPC
Class: |
C07C 29/40 20130101;
A01N 43/653 20130101; C07C 45/63 20130101; C07C 65/21 20130101;
C07C 235/44 20130101; C07C 29/40 20130101; C07D 249/08 20130101;
C07D 249/10 20130101; C07D 303/22 20130101; C07C 255/54 20130101;
A01N 2300/00 20130101; C07C 33/483 20130101; C07C 49/80 20130101;
C07C 45/63 20130101; A01N 43/653 20130101; A01N 43/707 20130101;
C07C 43/29 20130101; C07D 303/48 20130101; C07C 69/78 20130101 |
International
Class: |
A01N 43/707 20060101
A01N043/707; C07D 303/48 20060101 C07D303/48; C07C 69/78 20060101
C07C069/78; C07C 43/29 20060101 C07C043/29; C07C 235/44 20060101
C07C235/44; C07C 65/21 20060101 C07C065/21; C07D 249/08 20060101
C07D249/08; C07C 255/54 20060101 C07C255/54 |
Foreign Application Data
Date |
Code |
Application Number |
Nov 27, 2012 |
EP |
12194433.4 |
Jan 9, 2013 |
EP |
13150668.5 |
Claims
1-14. (canceled)
15. A compound of the formula I ##STR00026## wherein R.sup.1 is
selected from the group consisting of C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, phenyl, and
phenyl-C.sub.1-C.sub.4-alkyl; R.sup.2 is selected from the group
consisting of hydrogen, C.sub.1-C.sub.6=alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.2-C.sub.4-alkenyl and
phenyl-C.sub.2-C.sub.4-alkynyl wherein the aliphatic moieties of
R.sup.1 and/or R.sup.2 may carry one, two, three or up to the
maximum possible number of identical or different groups R.sup.12a
which independently of one another are selected from the group
consisting of: R.sup.12a is selected from the group consisting of
halogen, OH, CN, nitro, C.sub.1-C.sub.4-alkoxy,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and
C.sub.1-C.sub.4-halogenalkoxy; wherein the cycloalkyl and/or phenyl
moieties of R.sup.1 and/or R.sup.2 may carry one, two, three, four,
five or up to the maximum number of identical or different groups
R.sup.12b which independently of one another are selected from the
group consisting of: R.sup.12b is selected from the group
consisting of halogen, OH, CN, nitro, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and
C.sub.1-C.sub.4-halogenalkoxy R.sup.31 is halogen; R.sup.4 is
independently selected from the group consisting of halogen, CN,
NO.sub.2, OH, SH, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyloxy,
NH.sub.2, NH(C.sub.1-C.sub.4-alkyl),
N(C.sub.1-C.sub.4-alkyl).sub.2, NH(C.sub.3-C.sub.6-cycloalkyl),
N(C.sub.3-C.sub.6-cycloalkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)--(N(C.sub.3-C.sub.6-cycloalkyl).sub.2; wherein each of
R.sup.4 is unsubstituted or further substituted by one, two, three
or four R.sup.4a; wherein R.sup.4a is independently selected from
the group consisting of halogen, CN, NO.sub.2, OH,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl,
C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkox.sub.Y; p is 0,
1 or 2; m is 0, 1, 2, 3, 4 or 5; with the proviso that if m=1,
R.sup.4 is not para-halogen; with the proviso that if R.sup.31 is
Cl and m=2, (R.sup.4).sub.m is not 2,4-di-halogen, wherein each
halogen is selected from Cl and F; and with the proviso that if
R.sup.31 is Cl and m=3, (R.sup.4).sub.m is not 2,4,6-tri-halogen,
wherein each halogen is selected from Cl and F; and the N-oxides
and the agriculturally acceptable salts thereof.
16. The compound of claim 15, wherein m is 1 and R.sup.4 is in
ortho- or meta-position.
17. The compound of claim 15, wherein m is 2, 3 or 4 and two of the
R.sup.4 are in 2,3-, 3,4-, 3,5- or 2,6-position.
18. The compound of claim 15, wherein m is 2, 3 or 4 and two of the
R.sup.4, are in 2,4-position, wherein one (called R.sup.4-1) of
said two substituents is selected from the group consisting of CN,
NO.sub.2, OH, SH, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyloxy,
NH.sub.2, NH(C.sub.1-C.sub.4-alkyl),
N(C.sub.1-C.sub.4-alkyl).sub.2, NH(C.sub.3-C.sub.6-cycloalkyl),
N(C.sub.3-C.sub.6-cycloalkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)--(N(C.sub.3-C.sub.6-cycloalkyl).sub.2; wherein each
substituent is unsubstituted or further substituted by one, two,
three or four R.sup.4a; and wherein the other one (called
R.sup.4-2) is halogen or selected from the substituents as defined
for R.sup.4-1.
19. The compound of claim 15, wherein R.sup.31 is Br or F.
20. A composition comprising one compound of formula I, as defined
in claim 15, an N-oxide or an agriculturally acceptable salt
thereof.
21. The composition of claim 20, comprising additionally a further
active substance.
22. A method for combating harmful fungi, comprising treating the
fungi or the materials, plants, the soil or seeds to be protected
against fungal attack with an effective amount of at least one
compound of formula I, as defined in claim 15.
28. A method for combating harmful fungi, comprising treating the
fungi or the materials, plants, the soil or seeds to be protected
against fungal attack with an effective amount of the composition
of claim 20.
23. A seed coated with at least one compound of the formula I, as
defined in claim 15, and/or an agriculturally acceptable salt
thereof, in an amount of from 0.1 to 10 kg per 100 kg of seed.
29. A seed coated with the composition of claim 20 in an amount of
from 0.1 to 10 kg per 100 kg of seed.
24. A process (b) for the preparation of the compound of formula I
comprising the following step: 1b) reacting a compound of formula
Va ##STR00027## with an trimethylsulf(ox)onium halide, to obtain
the intermediate epoxide of formula IX: ##STR00028## wherein the
substituents are as defined in claim 15.
25. The process of claim 24, further comprising the step: 2b)
reacting a compound of formula IX as given in claim 24 with
R.sup.2OH in order to cleave the epoxide ring and to obtain
compounds of formula X ##STR00029##
26. The process of claim 25, further comprising the step: 2c)
reacting a compound of formula X as given in claim 25 with a
halogenating agent or sulfonating agent in order to introduce a
leaving group LG and to obtain compounds of formula XI:
##STR00030##
27. The intermediate compounds IX, X and XI of claim 26.
Description
[0001] The present invention relates to substituted [1,2,4]triazol
compounds and the N-oxides and the salts thereof for combating
phytopathogenic fungi, and to the use and methods for combating
phytopathogenic fungi and to seeds coated with at least one such
compound. The invention also relates to processes for preparing
these compounds, intermediates, processes for preparing such
intermediates, and to compositions comprising at least one compound
I.
[0002] EP 0 126 430 A2 relates to a process for the preparation of
1-triazolylethylether derivatives. EP 0 113 640 A2 relates to
1-azolyl-2-aryl-3-fluoroalkan-2-ols as microbiocides. DE 3801233
relates to 1-phenoxyphenyl-2-triazolyl-ethanolethers as
microbiocides. EP 0 275 955 A1 relates to
1-phenoxyphenyl-1-triazolylmethyl-carbinols as microbiocides. GB 2
130 584 A is directed to microbiocidal
1-carbonyl-1-phenoxyphenyl-2-azolylethanol-derivatives. WO
2013/010862 (PCT/EP2012/063526), WO 2013/010894
(PCT/EP2012/063635), WO 2013/010885 (PCT/EP2012/063620), WO
2013/024076 (PCT/EP2012/065835), WO 2013/024075
(PCT/EP2012/065834), WO 2013/024082 (PCT/EP2012/065850), WO
2013/024077 (PCT/EP2012/065836), WO 2013/024081
(PCT/EP2012/065848), WO 2013/024080 (PCT/EP2012/065847),
PCT/EP2012/065852 (PCT/EP2012/065852) and EP 2559688 (EP
11177556.5) are directed to specific fungicidal substituted
2-[2-halogen-4-phenoxyphenyl]-1-[1,2,4]triazol-1-yl-ethanol
compounds. EP 0 077 479 A2 relates to
phenoxyphenyl-azolylmethyl-ketons and -carbinols, processes for
their preparation and their use as intermediates and as fungicides.
EP 0 077 479 A2 does not contain any compound, wherein at the
"inner phenyl" a substituent corresponding to the inventive
R.sup.31 is present. EP 0 117 378 A1 is directed to
1-carbonyl-1-phenoxyphenyl-2-azolyl-ethynol derivatives and their
use as microbiocides. WO 2010/146114 A1 relates to triazole
compounds carrying a sulfur substituent and to precursors thereof.
J. Agric. Food. Chem. 2009, 57, 4854-4860 relates to the synthesis
and fungicidal evaluation of certain 2-arylphenyl
ether-3-(1H-1,2,4-triazol-1-yl)propan-2-ol derivatives. EP 0 440
950 A2 is directed to halgenallyl-azolyl-derivatives of the
formula
##STR00002##
wherein X.sup.1 and X.sup.2 are halogen and X.sup.3 is hydrogen or
halogen. CN 101225074 A relates to compounds
##STR00003##
i.e. to phenoxyphenyl substituted triazole compounds, wherein the
substituent corresponding to "R.sup.1" of the present invention is
phenylalkenyl.
[0003] In many cases, in particular at low application rates, the
fungicidal activity of the known fungicidal compounds is
unsatisfactory. Based on this, it was an object of the present
invention to provide compounds having improved activity and/or a
broader activity spectrum against phytopathogenic harmful
fungi.
[0004] Surprisingly, this object is achieved by the use of the
inventive substituted [1,2,4]triazol compounds of formula I having
favorable fungicidal activity against phytopathogenic fungi.
[0005] Accordingly, the present invention relates to the compounds
of formula I:
##STR00004##
wherein R.sup.1 is C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, phenyl or
phenyl-C.sub.1-C.sub.4-alkyl; R.sup.2 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.2-C.sub.4-alkenyl or
phenyl-C.sub.2-C.sub.4-alkynyl wherein the aliphatic moieties of
R.sup.1 and/or R.sup.2 may carry one, two, three or up to the
maximum possible number of identical or different groups R.sup.12a
which independently of one another are selected from: R.sup.12a
halogen, OH, CN, nitro, C.sub.1-C.sub.4-alkoxy,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and
C.sub.1-C.sub.4-halogenalkoxy; wherein the cycloalkyl and/or phenyl
moieties of R.sup.1 and/or R.sup.2 may carry one, two, three, four,
five or up to the maximum number of identical or different groups
R.sup.12b which independently of one another are selected from:
R.sup.12b halogen, OH, CN, nitro, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and
C.sub.1-C.sub.4-halogenalkoxy R.sup.31 is halogen; R.sup.4 is
independently selected from halogen, CN, NO.sub.2, OH, SH,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyloxy,
NH.sub.2, NH(C.sub.1-C.sub.4-alkyl),
N(C.sub.1-C.sub.4-alkyl).sub.2, NH(C.sub.3-C.sub.6-cycloalkyl),
N(C.sub.3-C.sub.6-cycloalkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)--(N(C.sub.3-C.sub.6-cycloalkyl).sub.2; wherein each of
R.sup.4 is unsubstituted or further substituted by one, two, three
or four R.sup.4a; wherein R.sup.4a is independently selected from
halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.4-alkoxy and
C.sub.1-C.sub.4-haloalkoxy; p is 0, 1 or 2; m is 0, 1, 2, 3, 4 or
5; with the proviso that if m=1, R.sup.4 is not para-halogen; with
the proviso that if R.sup.31 is Cl and m=2, (R.sup.4).sub.m is not
2,4-di-halogen, wherein each halogen is selected from Cl and F; and
with the proviso that if R.sup.31 is Cl and m=3, (R.sup.4).sub.m is
not 2,4,6-tri-halogen, wherein each halogen is selected from Cl and
F; and the N-oxides and the agriculturally acceptable salts
thereof.
[0006] In a particular embodiment, the provisos are as follows:
with the proviso that if m=1, R.sup.4 is not para-halogen; with the
proviso that if R.sup.31 is Cl and m=2, (R.sup.4).sub.m is not
2,4-di-halogen; and with the proviso that if R.sup.31 is Cl and
m=3, (R.sup.4).sub.m is not 2,4,6-tri-halogen; According to a more
particular embodiment, the provisos are as follows: with the
proviso that if m=1, R.sup.4 is not para-halogen; with the proviso
that if m=2, (R.sup.4).sub.m is not 2,4-di-halogen; and with the
proviso that if m=3, (R.sup.4).sub.m is not 2,4,6-tri-halogen.
[0007] The compounds according to the present invention
structurally differ from those described in the abovementioned
publications inter alia because of the specific substitution
pattern of the inner phenyl ring carrying only halogen as
ortho-R.sup.31 and no further substituents, in combination with the
specific substituents in the outer phenyl.
[0008] The compounds I can be obtained by various routes in analogy
to prior art processes known (cf. J. Agric. Food Chem. (2009) 57,
4854-4860; EP 0 275 955 A1; DE 40 03 180 A1; EP 0 113 640 A2; EP 0
126 430 A2) and by the synthesis routes shown in the following
schemes and in the experimental part of this application.
[0009] In a first process, for example, phenoles II are reacted, in
a first step, with derivatives IIIb, wherein X.sup.1 stands for I
or Br, in particular Br (=bromo derivatives III), preferably in the
presence of a base to result in compounds IVa.
##STR00005##
[0010] Thereafter, the resulting compounds IVa, in particular IV
(wherein X.sup.1 is Br) are then transformed into Grignard reagents
by the reaction with transmetallation reagents such as
isopropylmagnesium halides and subsequently reacted with acetyl
chloride preferably under anhydrous conditions and preferably in
the presence of a catalyst such as CuCl, CuCl.sub.2, AlCl.sub.3,
LiCl and mixtures thereof, in particular CuCl, to obtain
acetophenones V.
##STR00006##
[0011] These compounds V can be halogenated e.g. with bromine
preferably in an organic solvent such as diethyl ether, methyl
tert.-butyl ether (MTBE), methanol or acetic acid. In the resulting
compounds VI, "Hal" stands for "halogen" such as e.g. Br or Cl.
##STR00007##
[0012] Compounds VI can subsequently reacted with 1H-1,2,4-triazole
preferably in the presence of a solvent such as tetrahydrofuran
(THF), dimethylformamide (DMF), toluene, and in the presence of a
base such as potassium carbonate, sodium hydroxide or sodium
hydride to obtain compounds VII.
##STR00008##
[0013] These triazole keto compounds VII can be reacted with a
Grignard reagent such as R.sup.1MgBr or an organolithium reagent
R.sup.1Li preferably under anhydrous conditions to obtain compounds
I wherein R.sup.2 is hydrogen, which compounds are of formula I.1.
Optionally, a Lewis acid such as LaCl.sub.3x2 LiCl or
MgBr.sub.2xOEt.sub.2 can be used. If appropriate, these compounds
I.1 can subsequently be transformed e.g. with R.sup.2-LG, wherein
LG represents a nucleophilically replaceable leaving group such as
halogen, alkylsulfonyl, alkylsulfonyloxy and arylsulfonyloxy,
preferably chloro, bromo or iodo, particularly preferably bromo,
preferably in the presence of a base, such as for example, NaH in a
suitable solvent such as THF, to form other compounds I.
[0014] A second process to obtain the inventive compounds is as
follows:
[0015] In a first step, a halo derivative IIla, wherein X.sup.2 is
halogen, in particular F, and X.sup.3 is halogen, in particular Br,
is reacted with a transmetallation agent such as e.g.
isopropylmagnesium bromide followed by an acyl chloride agent
R.sup.1COCl (e.g. acetyl chloride) preferably under anhydrous
conditions and optionally in the presence of a catalyst such as
CuCl, CuCl.sub.2, AlCl.sub.3, LiCl and mixtures thereof, in
particular CuCl, to obtain ketones VIII.
##STR00009##
[0016] Thereafter, ketones VIII are reacted with phenoles II
preferably in the presence of a base to obtain compounds Va wherein
R.sup.1 is as defined and preferably defined, respectively,
herein.
##STR00010##
[0017] Compounds Va may also be obtained in analogy to the first
process described for compounds V (preferred conditions for the
process step, see above). This is illustrated as follows:
##STR00011##
[0018] Alternatively, compounds Va can be synthesized via a Friedel
Crafts acylation as follows:
##STR00012##
[0019] Ethers IVb can be synthesized by nucleophilic substitution
of X group in compound IIIc (Angewandte Chemie, International
Edition, 45(35), 5803-5807; 2006, US 20070088015 A1, Journal of the
American Chemical Society, 134(17), 7384-7391; 2012). Then, a Lewis
acid catalyzed addition of an acid halide, preferably will lead to
compounds Va (Journal of Chemical Research, Synopses, (8), 245;
1992, WO2010096777 A1).
[0020] Thereafter, intermediates Va are reacted with
trimethylsulf(ox)onium halides, preferably iodide, preferably in
the presence of a base such as sodium hydroxide.
##STR00013##
[0021] Thereafter, the epoxides IX are reacted with
1H-1,2,4-triazole preferably in the presence of a base such as
potassium carbonate and preferably in the presence of an organic
solvent such as DMF to obtain compounds I.1 (R.sup.2=hydrogen)
which may be further derivatized as described above.
[0022] In a third process, the epoxide ring of intermediates IX is
cleaved by reaction with alcohols R.sup.2OH preferably under acidic
conditions.
##STR00014##
[0023] Thereafter, the resulting compounds X are reacted with
halogenating agents or sulfonating agents such as PBr.sub.3,
PCl.sub.3 mesyl chloride, tosyl chloride or thionyl chloride, to
obtain compounds XI wherein LG is a nucleophilically replaceable
leaving group such as halogen, alkylsulfonyl, alkylsulfonyloxy and
arylsulfonyloxy, preferably chloro, bromo or iodo, particularly
preferably bromo or alkylsulfonyl. Then compounds XI are reacted
with 1H-1,2,4-triazole to obtain compounds I.
##STR00015##
[0024] Alternatively, compounds I can be prepared as follows:
##STR00016##
[0025] A halogenated compound XII, wherein X.sup.4.dbd.Br or I, is
transformed to the boronic acid or ester XIII (R''.dbd.H,
C.sub.1-C.sub.4-alkyl or R'' and R'' together form an optionally
(C.sub.1-C.sub.4)-alkyl-substituted #-CH.sub.2--CH.sub.2-# bridge,
such as #-C(CH.sub.3).sub.2--C(CH.sub.3).sub.2-#). For example,
KOAc, Pd(dppf)Cl.sub.2 and dioxane can be used in this step. A
reference for metallation, see Journal of the American Chemical
Society (2011), 133(40), 15800-15802; Journal of Organic Chemistry,
77(15), 6624-6628; 2012; Bioorganic & Medicinal Chemistry,
19(7), 2428-2442; 2011; Pd-catalyzed reaction: WO 2013041497 A1, US
2011449853P; Angewandte Chemie, International Edition (2010),
49(52), 10202-10205.
[0026] Those boronic compounds XIII can be oxidized to the
corresponding phenols XIV (see Journal of the American Chemical
Society, 130(30), 9638-9639; 2008; US 20080286812 A1; Tetrahedron,
69(30), 6213-6218; 2013; Tetrahedron Letters, 52(23), 3005-3008;
2011; WO 2003072100 A1).
##STR00017##
[0027] So obtained phenols XIV can be coupled with substituted
phenyl boronic acids to obtain the biphenyl ethers I (WO 2013014185
A1; Journal of Medicinal Chemistry, 55(21), 9120-9135; 2012;
Journal of Medicinal Chemistry, 54(6), 1613-1625; 2011; Bioorganic
& Medicinal Chemistry Letters, 15(1), 115-119; 2005; Bioorganic
& Medicinal Chemistry Letters, 17(6), 1799-1802; 2007). E.g.
Cu(OAc).sub.2 in CH.sub.2Cl.sub.2/MeCN can be used.
##STR00018##
[0028] If individual inventive compounds cannot be directly
obtained by the routes described above, they can be prepared by
derivatization of other inventive compounds.
[0029] The N-oxides may be prepared from the inventive compounds
according to conventional oxidation methods, e.g. by treating
compounds I with an organic peracid such as metachloroperbenzoic
acid (cf. WO 03/64572 or J. Med. Chem. 38(11), 1892-903, 1995); or
with inorganic oxidizing agents such as hydrogen peroxide (cf. J.
Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (cf. J. Am. Chem.
Soc. 123(25), 5962-5973, 2001). The oxidation may lead to pure
mono-N-oxides or to a mixture of different N-oxides, which can be
separated by conventional methods such as chromatography.
[0030] If the synthesis yields mixtures of isomers, a separation is
generally not necessarily required since in some cases the
individual isomers can be interconverted during work-up for use or
during application (e.g. under the action of light, acids or
bases). Such conversions may also take place after use, e.g. in the
treatment of plants in the treated plant, or in the harmful fungus
to be controlled.
[0031] In the following, the intermediate compounds are further
described. A skilled person will readily understand that the
preferences for the substituents given herein in connection with
compounds I apply for the intermediates accordingly. Thereby, the
substituents in each case have independently of each other or more
preferably in combination the meanings as defined herein.
[0032] Compounds of formula IVa and IV are partially new.
Consequently, a further embodiment of the present invention are
compounds of formula IVa and IV (see above), wherein the variables
R.sup.31, R.sup.4 and m are as defined and preferably defined for
formula I herein.
[0033] In specific embodiments of compounds IV and IVa according to
the present invention, the varia-bles R.sup.31, R.sup.4 and m are
as defined in Formulae I.A, I.B, I.C in combination with Table B
below, wherein each line of lines B-1 to B-146 of Table B
corresponds to one specific embodiment for R.sup.4 and m.
Furthermore, the substituents are specific embodiments
independently of each other or in any combination.
[0034] A further embodiment of the present invention is compounds
of formulae Va and V (see above), wherein the variables R.sup.1,
R.sup.31, R.sup.4 and m are as defined and preferably defined for
formula I herein.
[0035] In specific embodiments of compounds Va and V according to
the present invention, variables R.sup.1, R.sup.31, R.sup.4 and m
are as defined in Tables 1a to 70a, Tables 1b to 70b and Tables 1c
to 70c for compounds I, wherein the substituents are specific
embodiments independently of each other or in any combination.
[0036] A further embodiment of the present invention is compounds
of formula VI (see above), wherein variables R.sup.31, R.sup.4 and
m are as defined and preferably defined for formula I herein, and
wherein Hal stands for halogen, in particular Cl or Br. According
to one preferred embodiment, Hal in compounds VI stands for Br.
[0037] In specific embodiments of compounds VI according to the
present invention, the variables R.sup.31, R.sup.4 and m are as
defined in Formulae I.A, I.B, I.C in combination with Table B
below, wherein each line of lines B-1 to B-146 of Table B
corresponds to one specific embodiment for R.sup.4 and m.
Furthermore, the substituents are specific embodiments
independently of each other or in any combination.
[0038] A further embodiment of the present invention is compounds
of formula VII (see above), wherein the variables R.sup.31, R.sup.4
and m are as defined and preferably defined for formula I herein.
In specific embodiments of compounds VII according to the present
invention, the variables R.sup.31, R.sup.4 and m are as defined in
Formulae I.A, I.B, I.C in combination with Table B below, wherein
each line of lines B-1 to B-146 of Table B corresponds to one
specific embodiment for R.sup.4 and m. Furthermore, the
substituents are specific embodiments independently of each other
or in any combination.
[0039] A further embodiment of the present invention is compounds
of formula IX (see above), wherein the variables R.sup.1, R.sup.31,
R.sup.4 and m are as defined and preferably defined for formula I
herein. In specific embodiments of compounds IX according to the
present invention, the variables R.sup.1, R.sup.31, R.sup.4 and m
are as defined in Tables 1a to 70a, Tables 1b to 70b and Tables 1c
to 70c for compounds I, wherein the substituents are specific
embodiments independently of each other or in any combination.
[0040] A further embodiment of the present invention is compounds
of formula X, wherein the variables R.sup.1, R.sup.2, R.sup.31,
R.sup.4 and m are as defined and preferably defined for formula I
herein. In specific embodiments of compounds X according to the
present invention, the variables R.sup.1, R.sup.2, R.sup.31,
R.sup.4 and m are as defined in Tables 1a to 70a, Tables 1b to 70b
and Tables 1c to 70c for compounds I, wherein the substituents are
specific embodiments independently of each other or in any
combination.
[0041] A further embodiment of the present invention is compounds
of formula XI, wherein the variables R.sup.1, R.sup.2, R.sup.31,
R.sup.4 and m are as defined and preferably defined for formula I
herein, and LG stands for a leaving group as defined above.
[0042] In specific embodiments of compounds XI according to the
present invention, the variables R.sup.1, R.sup.2, R.sup.31,
R.sup.4 and m are as defined in Tables 1a to 70a, Tables 1b to 70b
and Tables 1c to 70c for compounds I, wherein the substituents are
specific embodiments independently of each other or in any
combination.
[0043] In the definitions of the variables given above, collective
terms are used which are generally representative for the
substituents in question. The term "C.sub.n-C.sub.m" indicates the
number of carbon atoms possible in each case in the substituent or
substituent moiety in question.
[0044] The term "halogen" refers to fluorine, chlorine, bromine and
iodine.
[0045] The term "C.sub.1-C.sub.6-alkyl" refers to a
straight-chained or branched saturated hydrocarbon group having 1
to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl,
butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,
1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,
1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl,
1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,
1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,
1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and
1-ethyl-2-methylpropyl. Likewise, the term "C.sub.1-C.sub.4-alkyl"
refers to a straight-chained or branched alkyl group having 1 to 4
carbon atoms, such as methyl, ethyl, propyl(n-propyl),
1-methylethyl(iso-propoyl), butyl, 1-methylpropyl(sec.-butyl),
2-methylpropyl(iso-butyl), 1,1-dimethylethyl(tert.butyl). Likewise,
the term "C.sub.2-C.sub.4-alkyl" refers to a straight-chained or
branched alkyl group having 2 to 4 carbon atoms, such as ethyl,
propyl(n-propyl), 1-methylethyl(iso-propoyl), butyl,
1-methylpropyl(sec.-butyl), 2-methylpropyl(iso-butyl),
1,1-dimethylethyl(tert.-butyl).
[0046] The term "C.sub.1-C.sub.6-haloalkyl" refers to an alkyl
group having 1 or 6 carbon atoms as defined above, wherein some or
all of the hydrogen atoms in these groups may be replaced by
halogen atoms as mentioned above. Examples are
"C.sub.1-C.sub.2-haloalkyl" groups such as chloromethyl,
bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,
difluoromethyl, trifluoromethyl, chlorofluoromethyl,
dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl,
1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,
2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,
2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,
2,2,2-trichloroethyl or pentafluoroethyl.
[0047] The term "C.sub.2-C.sub.6-alkenyl" refers to a
straight-chain or branched unsaturated hydrocarbon radical having 2
to 6 carbon atoms and a double bond in any position. Examples are
"C.sub.2-C.sub.4-alkenyl" groups, such as ethenyl, 1-propenyl,
2-propenyl(allyl), 1-methylethenyl, 1-butenyl, 2-butenyl,
3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,
1-methyl-2-propenyl, 2-methyl-2-propenyl.
[0048] The term "C.sub.2-C.sub.6-alkynyl" refers to a
straight-chain or branched unsaturated hydrocarbon radical having 2
to 6 carbon atoms and containing at least one triple bond. Examples
are "C.sub.2-C.sub.4-alkynyl" groups, such as ethynyl, prop-1-ynyl,
prop-2-ynyl(propargyl), but-1-ynyl, but-2-ynyl, but-3-ynyl,
1-methyl-prop-2-ynyl.
[0049] The term "C.sub.3-C.sub.8-cycloalkyl" refers to monocyclic
saturated hydrocarbon radicals having 3 to 8 carbon ring members,
such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
cycloheptyl or cyclooctyl.
[0050] The term "C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl"
refers to alkyl having 1 to 4 carbon atoms (as defined above),
wherein one hydrogen atom of the alkyl radical is replaced by a
cycloalkyl radical having 3 to 8 carbon atoms (as defined
above).
[0051] The term "C.sub.1-C.sub.6-alkoxy" refers to a straight-chain
or branched alkyl group having 1 to 6 carbon atoms which is bonded
via an oxygen, at any position in the alkyl group. Examples are
"C.sub.1-C.sub.4-alkoxy" groups, such as methoxy, ethoxy,
n-propoxy, 1-methylethoxy, butoxy, 1-methyl-propoxy,
2-methylpropoxy or 1,1-dimethylethoxy. Likewise, the term
"C.sub.1-C.sub.4-alkoxy" refers to a straight-chain or branched
alkyl group having 1 to 4 carbon atoms which is bonded via an
oxygen, at any position in the alkyl group, examples are methoxy,
ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methyl-propoxy,
2-methylpropoxy or 1,1-dimethylethoxy.
[0052] The term "C.sub.1-C.sub.6-haloalkoxy" refers to a
C.sub.1-C.sub.6-alkoxy radical as defined above, wherein some or
all of the hydrogen atoms in these groups may be replaced by
halogen atoms as mentioned above. Examples are
"C.sub.1-C.sub.4-haloalkoxy" groups, such as OCH.sub.2F,
OCHF.sub.2, OCF.sub.3, OCH.sub.2Cl, OCHCl.sub.2, OCCl.sub.3,
chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,
2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy,
2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,
2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2,2,2-trichloro-ethoxy, 0C.sub.2F.sub.5, 2-fluoropropoxy,
3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoro-'propoxy, 2
chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy,
2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy,
3,3,3-trichloropropoxy, OCH.sub.2--C.sub.2F.sub.5,
OCF.sub.2--C.sub.2F.sub.5, 1-fluoromethyl-2-fluoroethoxy,
1-chloromethyl-2-chloroethoxy, 1-bromomethyl-2-bromo'ethoxy,
4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or
nonafluorobutoxy.
[0053] The term "phenyl-C.sub.1-C.sub.6-alkyl" refers to alkyl
having 1 to 6 carbon atoms (as defined above), wherein one hydrogen
atom of the alkyl radical is replaced by a phenyl radical.
Likewise, the terms "phenyl-C.sub.2-C.sub.6-alkenyl" and
"phenyl-C.sub.2-C.sub.6-alkynyl" refer to alkenyl and alkynyl,
respectively, wherein one hydrogen atom of the aforementioned
radicals is replaced by a phenyl radical.
[0054] The term "C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl"
refers to alkyl having 1 to 6 carbon atoms (as defined above),
wherein one hydrogen atom of the alkyl radical is replaced by a
C.sub.1-C.sub.4-alkoxy radical having 1 to 4 carbon atoms (as
defined above).
[0055] The term "C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.6-alkenyl"
refers to alkenyl having 2 to 6 carbon atoms (as defined above),
wherein one hydrogen atom of the alkenyl radical is replaced by a
C.sub.1-C.sub.4-alkoxy radical having 1 to 4 carbon atoms (as
defined above).
[0056] The term "C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.6-alkynyl"
refers to alkynyl having 2 to 6 carbon atoms (as defined above),
wherein one hydrogen atom of the alkynyl radical is replaced by a
C.sub.1-C.sub.4-alkoxy radical having 1 to 4 carbon atoms (as
defined above).
[0057] Agriculturally acceptable salts of the inventive compounds
encompass especially the salts of those cations or the acid
addition salts of those acids whose cations and anions,
respectively, have no adverse effect on the fungicidal action of
said compounds. Suitable cations are thus in particular the ions of
the alkali metals, preferably sodium and potassium, of the alkaline
earth metals, preferably calcium, magnesium and barium, of the
transition metals, preferably manganese, copper, zinc and iron, and
also the ammonium ion which, if desired, may carry one to four
C.sub.1-C.sub.4-alkyl substituents and/or one phenyl or benzyl
substituent, preferably diisopropylammonium, tetramethylammonium,
tetrabutylammonium, trimethylbenzylammonium, furthermore
phosphonium ions, sulfonium ions, preferably
tri(C.sub.1-C.sub.4-alkyl)sulfonium, and sulfoxonium ions,
preferably tri(C.sub.1-C.sub.4-alkyl)sulfoxonium. Anions of useful
acid addition salts are primarily chloride, bromide, fluoride,
hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate,
phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,
hexafluorophosphate, benzoate, and the anions of
C.sub.1-C.sub.4-alkanoic acids, preferably formate, acetate,
propionate and butyrate. They can be formed by reacting such
inventive compound with an acid of the corresponding anion,
preferably of hydrochloric acid, hydrobromic acid, sulfuric acid,
phosphoric acid or nitric acid.
[0058] The inventive compounds can be present in atropisomers
arising from restricted rotation about a single bond of asymmetric
groups. They also form part of the subject matter of the present
invention.
[0059] Depending on the substitution pattern, the compounds of
formula I and their N-oxides may have one or more centers of
chirality, in which case they are present as pure enantiomers or
pure diastereomers or as enantiomer or diastereomer mixtures. Both,
the pure enantiomers or diastereomers and their mixtures are
subject matter of the present invention.
[0060] In the following, particular embodiments of the inventive
compounds are described. Therein, specific meanings of the
respective substituents are further detailled, wherein the meanings
are in each case on their own but also in any combination with one
another, particular embodiments of the present invention.
[0061] Furthermore, in respect of the variables, generally, the
embodiments of the compounds I also apply to the intermediates.
[0062] R.sup.1 according to the present invention is
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, phenyl or
phenyl-C.sub.1-C.sub.4-alkyl, wherein the aliphatic moieties of
R.sup.1 may carry one, two, three or up to the maximum possible
number of identical or different groups R.sup.12a which
independently of one another are selected from halogen, OH, CN,
nitro, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl and C.sub.1-C.sub.4-halogenalkoxy;
and wherein the cycloalkyl and/or phenyl moieties of R.sup.1 may
carry one, two, three, four, five or up to the maximum number of
identical or different groups R.sup.12b, which independently of one
another are selected from halogen, OH, CN, nitro,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl and
C.sub.1-C.sub.4-halogenalkoxy.
[0063] According to one embodiment, R.sup.1 is
C.sub.1-C.sub.6-alkyl, CF.sub.3, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-haloalkenyl,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.1-C.sub.4-haloalkyl and
phenyl-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, wherein the
aliphatic moieties of R.sup.1 are not further substituted or carry
one, two, three or up to the maximum possible number of identical
or different groups R.sup.12a1 which independently of one another
are selected from OH, CN, nitro, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl and C.sub.1-C.sub.4-halogenalkoxy;
and wherein the cycloalkyl and/or phenyl moieties of R.sup.1 may
carry one, two, three, four, five or up to the maximum number of
identical or different groups R.sup.12b which independently of one
another are selected from halogen, OH, CN, nitro,
C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl and C.sub.1-C.sub.4-halogenalkoxy.
According to a further embodiment, R.sup.1 is
C.sub.1-C.sub.6-alkyl, CF.sub.3, C.sub.2-C.sub.6-alkenyl,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.1-C.sub.4-haloalkyl and
phenyl-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, wherein the
aliphatic moieties of R.sup.1 are not further substituted or carry
one, two, three or up to the maximum possible number of identical
or different groups R.sup.12a1 which independently of one another
are selected from OH, CN, nitro, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl and C.sub.1-C.sub.4-halogenalkoxy;
and wherein the cycloalkyl and/or phenyl moieties of R.sup.1 may
carry one, two, three, four, five or up to the maximum number of
identical or different groups R.sup.12b which independently of one
another are selected from halogen, OH, CN, nitro,
C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl and
C.sub.1-C.sub.4-halogenalkoxy.
[0064] According to a further embodiment of the invention, R.sup.1
is selected from C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl and
phenyl-C.sub.1-C.sub.4-alkyl, wherein the R.sup.1 are in each case
unsubstituted or are substituted by R.sup.12a and/or R.sup.12b as
defined and preferably defined herein. Specific embodiments thereof
can be found in the below Table P1.
[0065] According to one particular embodiment, R.sup.1 is
C.sub.1-C.sub.6-alkyl, in particular C.sub.1-C.sub.4-alkyl, such as
CH.sub.3, C.sub.2H.sub.5, CH(CH.sub.3).sub.2 or C(CH.sub.3).sub.3.
According to one embodiment, this R.sup.1 is not further
substituted. A further embodiment relates to compounds, wherein
R.sup.1 is C.sub.1-C.sub.6-alkyl, in particular
C.sub.1-C.sub.4-alkyl, that is substituted by one, two or three or
up to the maximum possible number of identical or different groups
R.sup.12a, as defined and preferably defined herein. According to a
specific embodiment thereof, R.sup.1 is C.sub.1-C.sub.6-haloalkyl,
in particular C.sub.1-C.sub.4-haloalkyl, more particularly
C.sub.1-C.sub.2-haloalkyl such as CF.sub.3 or CHF.sub.2. According
to a further specific embodiment thereof, R.sup.1 is
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl, in particular
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, such as
CH.sub.2--OCH.sub.3. Further specific embodiments thereof can be
found in the below Table P1.
[0066] According to still another embodiment, R.sup.1 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, in particular
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl. A further
embodiment relates to compounds, wherein R.sup.1 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, in particular
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, that is
substituted by one, two or three or up to the maximum possible
number of identical or different groups R.sup.12a in the alkyl
moiety and/or substituted by one, two, three four or five or up to
the maximum possible number of identical or different groups
R.sup.12b in the cycloalkyl moiety. R.sup.12a and R.sup.12b are in
each case as defined and preferably defined herein. Specific
embodiments thereof can be found in the below Table P1.
[0067] According to another embodiment, R.sup.1 is
C.sub.2-C.sub.6-alkenyl, in particular C.sub.2-C.sub.4-alkenyl,
such as CH.dbd.CH.sub.2, CH.sub.2CH.dbd.CH.sub.2, CH.dbd.CHCH.sub.3
or C(CH.sub.3).dbd.CH.sub.2. According to one embodiment, if
R.sup.1 is alkenyl, said alkenyl is not substituted. A further
embodiment relates to compounds, wherein R.sup.1 is
C.sub.2-C.sub.6-alkenyl, in particular C.sub.2-C.sub.4-alkenyl,
that is substituted by one, two or three or up to the maximum
possible number of identical or different groups R.sup.12a as
defined and preferably defined herein. According to a specific
embodiment thereof, R.sup.1 is C.sub.2-C.sub.6-haloalkenyl, in
particular C.sub.2-C.sub.4-haloalkenyl, wherein specifically, said
haloalkenyl contains exactly one halogen. According to a further
specific embodiment thereof, R.sup.1 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.6-alkenyl or
C.sub.3-C.sub.8-halocycloalkyl-C.sub.2-C.sub.6-alkenyl, in
particular C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.4-alkenyl or
C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.4-alkenyl. Further
specific embodiments thereof can be found in the below Table
P1.
[0068] According to still another embodiment, R.sup.1 is
C.sub.2-C.sub.6-alkynyl, in particular C.sub.2-C.sub.4-alkynyl,
such as C.ident.CH, CC.ident.CH.sub.3, CH.sub.2--C.ident.C--H or
CH.sub.2--C.ident.C--CH.sub.3. A further embodiment relates to
compounds, wherein R.sup.1 is C.sub.2-C.sub.6-alkynyl, in
particular C.sub.2-C.sub.4-alkynyl, that is substituted by one, two
or three or up to the maximum possible number of identical or
different groups R.sup.12a, as defined and preferably defined
herein. According to a specific embodiment thereof, R.sup.1 is
C.sub.2-C.sub.6-haloalkynyl, in particular
C.sub.2-C.sub.4-haloalkynyl. According to a further specific
embodiment thereof, R.sup.1 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.6-alkynyl or
C.sub.3-C.sub.8-halocycloalkyl-C.sub.2-C.sub.6-alkynyl, in
particular C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.4-alkynyl or
C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.4-alkynyl. Further
specific embodiments thereof can be found in the below Table
P1.
[0069] According to still another embodiment, R.sup.1 is
phenyl-C.sub.1-C.sub.4-alkyl, in particular
phenyl-C.sub.1-C.sub.2-alkyl, such as benzyl, wherein the alkyl
moiety in each case is unsubstituted or carries one, two or three
R.sup.12a as defined and preferably defined herein, in particular
selected from halogen, in particular F and Cl,
C.sub.1-C.sub.4-alkoxy, in particular OCH.sub.3, and CN, and
wherein the phenyl in each case is unsubstituted or carries one,
two or three R.sup.12b as as defined and preferably defined herein,
in particular selected from halogen, in particular Cl and F,
C.sub.1-C.sub.4-alkoxy, in particular OCH.sub.3,
C.sub.1-C.sub.4-alkyl, in particular CH.sub.3 or C.sub.2H.sub.5,
and CN. Specific embodiments thereof can be found in the below
Table P1.
[0070] According to still another embodiment, R.sup.1 is
C.sub.3-C.sub.8-cycloalkyl, in particular
C.sub.3-C.sub.6-cycloalkyl, such as C.sub.3H.sub.5 (cyclopropyl),
C.sub.4H.sub.7 (cyclobutyl), cyclopentyl or cyclohexyl. A further
embodiment relates to compounds, wherein R.sup.1 is
C.sub.3-C.sub.8-cycloalkyl, in particular
C.sub.3-C.sub.6-cycloalkyl, such as C.sub.3H.sub.5 (cyclopropyl) or
C.sub.4H.sub.7 (cyclobutyl), that is substituted by one, two, three
four or five or up to the maximum possible number of identical or
different groups R.sup.12b as defined and preferably defined
herein. According to a specific embodiment thereof, R.sup.1 is
C.sub.3-C.sub.8-halocycloalkyl, in particular
C.sub.3-C.sub.6-halocycloalkyl, such as halocyclopropyl, in
particular 1-F-cyclopropyl or 1-C.sub.1-cyclopropyl. According to a
further specific embodiment thereof, R.sup.1 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.3-C.sub.8-cycloalkyl, in
particular C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-cycloalkyl,
wherein each of said cycloalkylcycloalkyl moieties is unsubstituted
or carries one, two or three R.sup.12b as defined and preferably
defined herein, such as 1-cyclopropyl-cyclopropyl or
2-cyclopropyl-cyclopropyl. Specific embodiments thereof can be
found in the below Table P1.
[0071] According to still another embodiment, R.sup.1 is phenyl,
wherein the phenyl is unsubstituted or carries one, two, three,
four or five independently selected R.sup.12b as defined and
preferably defined herein, in particular selected from halogen, in
particular Cl and F, C.sub.1-C.sub.4-alkoxy, in particular
OCH.sub.3, C.sub.1-C.sub.4-alkyl, in particular CH.sub.3 or
C.sub.2H.sub.5, and CN. Specific embodiments thereof can be found
in the below Table P1.
[0072] In a further embodiment of the invention, R.sup.1 is
selected from C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl and C.sub.3-C.sub.6-cycloalkyl, wherein the
R.sup.1 are in each case unsubstituted or are substituted by
R.sup.12a and/or R.sup.12b as defined and preferably defined
herein. In each case, the substituents may also have the preferred
meanings for the respective substituent as defined above. Specific
embodiments thereof can be found in the below Table P1.
[0073] In still a further embodiment of the invention, R.sup.1 is
selected from C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl and
C.sub.3-C.sub.6-cycloalkyl, wherein the R.sup.1 are in each case
unsubstituted or are substituted by R.sup.12a1 and/or R.sup.12b as
defined and preferably defined herein. In each case, the
substituents may also have the preferred meanings for the
respective substituent as defined above. Specific embodiments
thereof can be found in the below Table P1. Particularly preferred
embodiments of R.sup.1 according to the invention are in Table P1
below, wherein each line of lines P1-1 to P1-160 corresponds to one
particular embodiment of the invention, wherein P1-1 to P1-160 are
also in any combination a preferred embodiment of the present
invention.
TABLE-US-00001 TABLE P1 line R.sup.1 P1-1 H P1-2 CH.sub.3 P1-3
CH.sub.2CH.sub.3 P1-4 CH.sub.2CH.sub.2CH.sub.3 P1-5
CH(CH.sub.3).sub.2 P1-6 C(CH.sub.3).sub.3 P1-7
CH(CH.sub.3)CH.sub.2CH.sub.3 P1-8 CH.sub.2CH(CH.sub.3).sub.2 P1-9
CH.sub.2CH.sub.2CH.sub.2CH.sub.3 P1-10 CF.sub.3 P1-11 CHF.sub.2
P1-12 CH.sub.2F P1-13 CHCl.sub.2 P1-14 CH.sub.2Cl P1-15 CH.sub.2OH
P1-16 CH.sub.2CH.sub.2OH P1-17 CH.sub.2CH.sub.2CH.sub.2OH P1-18
CH(CH.sub.3)CH.sub.2OH P1-19 CH.sub.2CH(CH.sub.3)OH P1-20
CH.sub.2CH.sub.2CH.sub.2CH.sub.2OH P1-21 CH(CH.sub.3)CN P1-22
CH.sub.2CH.sub.2CN P1-23 CH.sub.2CN P1-24 CH.sub.2CH.sub.2CN P1-25
CH.sub.2CH.sub.2CH.sub.2CN, P1-26 CH(CH.sub.3)CH.sub.2CN P1-27
CH.sub.2CH(CH.sub.3)CN P1-28 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN
P1-29 CH.sub.2OCH.sub.3 P1-30 CH.sub.2OCH.sub.2CH.sub.3 P1-31
CH(CH.sub.3)OCH.sub.3 P1-32 CH(CH.sub.3)OCH.sub.2CH.sub.3 P1-33
CH.sub.2CH.sub.2OCH.sub.2CH.sub.3 P1-34 CH.sub.2OCF.sub.3 P1-35
CH.sub.2CH.sub.2OCF.sub.3 P1-36 CH.sub.2OCCl.sub.3 P1-37
CH.sub.2CH.sub.2OCCl.sub.3 P1-38 CH.dbd.CH.sub.2 P1-39
CH.sub.2CH.dbd.CH.sub.2 P1-40 CH.sub.2CH.dbd.CHCH.sub.3 P1-41
CH.sub.2C(CH.sub.3).dbd.CH.sub.2 P1-42
CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 P1-43
CH.sub.2C(CH.sub.3).dbd.C(CH.sub.3).sub.2 P1-44 CH.dbd.CHCH.sub.3
P1-45 C(CH.sub.3).dbd.CH.sub.2 P1-46 CH.dbd.C(CH.sub.3).sub.2 P1-47
C(CH.sub.3).dbd.C(CH.sub.3).sub.2 P1-48
C(CH.sub.3).dbd.CH(CH.sub.3) P1-49 C(Cl).dbd.CH.sub.2 P1-50
C(H).dbd.CHCl P1-51 C(Cl).dbd.CHCl P1-52 CH.dbd.CCl.sub.2 P1-53
C(Cl).dbd.CCl.sub.2 P1-54 C(H).dbd.CH(F) P1-55 C(H).dbd.CF.sub.2
P1-56 C(F).dbd.CF.sub.2 P1-57 C(F).dbd.CHF P1-58
CH.dbd.CHCH.sub.2OH P1-59 CH.dbd.CHOCH.sub.3 P1-60
CH.dbd.CHCH.sub.2OCH.sub.3 P1-61 CH.dbd.CHCH.sub.2OCF.sub.3 P1-62
CH.dbd.CHCH.sub.2OCCl.sub.3 P1-63 CH.dbd.CH(C.sub.3H.sub.5) P1-64
CH.dbd.CH(C.sub.4H.sub.7) P1-65 CH.dbd.CH(1-Cl--C.sub.3H.sub.4)
P1-66 CH.dbd.CH(1-F--C.sub.3H.sub.4) P1-67
CH.dbd.CH(1-Cl--C.sub.4H.sub.6) P1-68
CH.dbd.CH(1-F--C.sub.4H.sub.6) P1-69 C.ident.CH P1-70
C.ident.CCH.sub.3 P1-71 CH.sub.2C.ident.CCH.sub.3 P1-72
CH.sub.2C.ident.CH P1-73 CH.sub.2C.ident.CCH.sub.2CH.sub.3 P1-74
C.ident.CCH(CH.sub.3).sub.2 P1-75 C.ident.CC(CH.sub.3).sub.3 P1-76
C.ident.C(C.sub.3H.sub.5) P1-77 C.ident.C(C.sub.4H.sub.7) P1-78
C.ident.C(1-Cl--C.sub.3H.sub.4) P1-79
C.ident.C(1-Cl--C.sub.4H.sub.6) P1-80 C.ident.CCl P1-81 C.ident.CBr
P1-82 C.ident.C--I P1-83 CH.sub.2C.ident.CCl P1-84
CH.sub.2C.ident.CBr P1-85 CH.sub.2C.ident.C--I P1-86
C.ident.CCH.sub.2OCH.sub.3 P1-87 C.ident.CCH(OH)CH.sub.3 P1-88
C.ident.CCH(OCH.sub.3)CH.sub.3 P1-89 C.ident.COCH.sub.3 P1-90
CH.sub.2C.ident.COCH.sub.3 P1-91 C.ident.CCH.sub.2OCCl.sub.3 P1-92
C.ident.CCH.sub.2OCF.sub.3 P1-93 C.ident.CCH.sub.2(C.sub.3H.sub.5)
P1-94 C.ident.CCH.sub.2(C.sub.4H.sub.7) P1-95
C.ident.C(1-Cl--C.sub.3H.sub.4) P1-96
C.ident.C(1-F--C.sub.3H.sub.4) P1-97
C.ident.C(1-Cl--C.sub.4H.sub.6) P1-98
C.ident.C(1-F--C.sub.4H.sub.6) P1-99 C.sub.3H.sub.5 (cyclopropyl)
P1-100 C.sub.4H.sub.7 (cyclobutyl) P1-101 C.sub.5H.sub.9
(cyclopentyl) P1-102 cyclohexyl P1-103 CH(CH.sub.3)--C.sub.3H.sub.5
(CH(CH.sub.3)-cyclopropyl) P1-104 CH.sub.2--C.sub.3H.sub.5
(CH.sub.2-cyclopropyl) P1-105 1-(Cl)-cyclopropyl P1-106
1-(F)-cyclopropyl P1-107 1-(CH.sub.3)-cyclopropyl P1-108
1-(CN)-cyclopropyl P1-109 2-(Cl)-cyclopropyl P1-110
2-(F)-cyclopropyl P1-111 1-(Cl)-cyclobutyl P1-112 1-(F)-cyclobutyl
P1-113 2-(Cl)-cyclobutyl P1-114 3-(Cl)-cyclobutyl P1-115
2-(F)-cyclobutyl P1-116 3-(F)-cyclobutyl P1-117
3,3-Cl.sub.2-cyclobutyl P1-118 3,3-F.sub.2-cyclobutyl P1-119
2-(CH.sub.3)-cyclopropyl P1-120 1-(CH.sub.3)-cyclobutyl P1-121
2-(CH.sub.3)-cyclobutyl P1-122 3-(CH.sub.3)-cyclobutyl P1-123
3,3-(CH.sub.3).sub.2-cyclobutyl P1-124 2-(CN)-cyclopropyl P1-125
1-cyclopropyl-cyclopropyl P1-126 2-cyclopropyl-cyclopropyl P1-127
CH(CH.sub.3)(cyclobutyl) P1-128 CH.sub.2-(cyclobutyl) P1-129
CH.sub.2CH.sub.2-(cyclopropyl) P1-130 CH.sub.2CH.sub.2-(cyclobutyl)
P1-131 CH.sub.2-(1-Cl-cyclopropyl) P1-132
CH.sub.2-(1-F-cyclopropyl) P1-133 CH.sub.2-(1-Cl-cyclobutyl) P1-134
CH.sub.2-(1-F-cyclobutyl) P1-135 CHCH.sub.3-(1-Cl-cyclopropyl)
P1-136 C(CH.sub.3).sub.2-(1-F-cyclopropyl) P1-137 C.sub.6H.sub.5
P1-138 4-Cl--C.sub.6H.sub.4 P1-139 4-OCH.sub.3--C.sub.6H.sub.4
P1-140 4-CH.sub.3--C.sub.6H.sub.4 P1-141 4-F--C.sub.6H.sub.4 P1-142
2,4-F.sub.2--C.sub.6H.sub.3 P1-143 2,4-Cl.sub.2--C.sub.6H.sub.3
P1-144 2-CH.sub.3--C.sub.6H.sub.4 P1-145 2-CF.sub.3--C.sub.6H.sub.4
P1-146 4-CH.sub.3--C.sub.6H.sub.4 P1-147 4-CF.sub.3--C.sub.6H.sub.4
P1-148 2-OCH.sub.3--C.sub.6H.sub.4 P1-149
2-OCF.sub.3--C.sub.6H.sub.4 P1-150 4-OCH.sub.3--C.sub.6H.sub.4
P1-151 4-OCF.sub.3--C.sub.6H.sub.4 P1-152
2,4,6-F.sub.3--C.sub.6H.sub.2 P1-153 2,4,6-Cl.sub.3--C.sub.6H.sub.2
P1-154 CH.sub.2C.sub.6H.sub.5 P1-155
CH.sub.2--(4-Cl)--C.sub.6H.sub.4 P1-156
CH.sub.2--(4-CH.sub.3)--C.sub.6H.sub.4 P1-157
CH.sub.2--(4-OCH.sub.3)--C.sub.6H.sub.4 P1-158
CH.sub.2--(4-F)--C.sub.6H.sub.4 P1-159
CH.sub.2-(2,4-Cl.sub.2)--C.sub.6H.sub.3 P1-160
CH.sub.2-(2,4-F.sub.2)--C.sub.6H.sub.3
R.sup.2 according to the present invention is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.2-C.sub.4-alkenyl or
phenyl-C.sub.2-C.sub.4-alkynyl, wherein the aliphatic groups of
R.sup.2 may carry one, two, three or up to the maximum possible
number of identical or different groups R.sup.12a which
independently of one another are selected from halogen, OH, CN,
nitro, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl and C.sub.1-C.sub.4-halogenalkoxy;
and wherein the cycloalkyl and/or phenyl moieties of R.sup.2 may
carry one, two, three, four, five or up to the maximum number of
identical or different groups R.sup.12b, which independently of one
another are selected from halogen, OH, CN, nitro,
C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl and
C.sub.1-C.sub.4-halogenalkoxy.
[0074] According to one embodiment, R.sup.2 is H.
[0075] According to a further embodiment of the invention, R.sup.2
is selected from C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.2-C.sub.4-alkenyl and
phenyl-C.sub.2-C.sub.4-alkynyl, wherein the R.sup.2 are in each
case unsubstituted or are substituted by R.sup.12a and/or R.sup.12b
as defined and preferably defined herein. Specific embodiments
thereof can be found in the below Table P2.
[0076] According to one particular embodiment, R.sup.2 is
C.sub.1-C.sub.6-alkyl, in particular C.sub.1-C.sub.4-alkyl, such as
CH.sub.3, C.sub.2H.sub.5, CH(CH.sub.3).sub.2,
CH.sub.2CH.sub.2CH.sub.3, CH.sub.2CH.sub.2CH.sub.2CH.sub.3,
CH.sub.2CH(CH.sub.3).sub.2. A further embodiment relates to
compounds, wherein R.sup.2 is C.sub.1-C.sub.6-alkyl, in particular
C.sub.1-C.sub.4-alkyl, that is substituted by one, two or three or
up to the maximum possible number of identical or different groups
R.sup.12a, as defined and preferably defined herein. According to a
specific embodiment thereof, R.sup.2 is C.sub.1-C.sub.6-haloalkyl,
in particular C.sub.1-C.sub.4-haloalkyl, more particularly
C.sub.1-C.sub.2-haloalkyl. According to a further specific
embodiment thereof, R.sup.2 is
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl, in particular
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, such as
CH.sub.2OCH.sub.3 or CH.sub.2CH.sub.2OCH.sub.3. According to still
a further specific embodiment thereof, R.sup.2 is
hydroxy-C.sub.1-C.sub.6-alkyl, in particular
hydroxyl-C.sub.1-C.sub.4-alkyl, such as CH.sub.2CH.sub.2OH. Further
specific embodiments thereof can be found in the below Table P2
[0077] According to still another embodiment, R.sup.2 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, in particular
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl. A further
embodiment relates to compounds, wherein R.sup.2 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.6-alkyl, in particular
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, more particularly
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.2-alkyl, that is
substituted by one, two or three or up to the maximum possible
number of identical or different groups R.sup.12a in the alkyl
moiety and/or substituted by one, two, three four or five or up to
the maximum possible number of identical or different groups
R.sup.12b in the cycloalkyl moiety. R.sup.12a and R.sup.12b are in
each case as defined and preferably defined herein. Specific
embodiments thereof can be found in the below Table P2.
[0078] According to another embodiment, R.sup.2 is
C.sub.2-C.sub.6-alkenyl, in particular C.sub.2-C.sub.4-alkenyl,
such as CH.sub.2CH.dbd.CH.sub.2, CH.sub.2C(CH.sub.3).dbd.CH.sub.2
or CH.sub.2CH.dbd.CHCH.sub.3. A further embodiment relates to
compounds, wherein R.sup.2 is C.sub.2-C.sub.6-alkenyl, in
particular C.sub.2-C.sub.4-alkenyl, that is substituted by one, two
or three or up to the maximum possible number of identical or
different groups R.sup.12a as defined and preferably defined
herein. According to a specific embodiment thereof, R.sup.2 is
C.sub.2-C.sub.6-haloalkenyl, in particular
C.sub.2-C.sub.4-haloalkenyl, such as CH.sub.2C(Cl).dbd.CH.sub.2 and
CH.sub.2C(H).dbd.CHCl. According to a further specific embodiment
thereof, R.sup.2 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.6-alkenyl or
C.sub.3-C.sub.8-halocycloalkyl-C.sub.2-C.sub.6-alkenyl, in
particular C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.4-alkenyl or
C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.4-alkenyl. Further
specific embodiments thereof can be found in the below Table
P2.
[0079] According to still another embodiment, R.sup.2 is
C.sub.2-C.sub.6-alkynyl, in particular C.sub.2-C.sub.4-alkynyl,
such as CH.sub.2C.ident.CH or CH.sub.2C.ident.CCH.sub.3. A further
embodiment relates to compounds, wherein R.sup.2 is
C.sub.2-C.sub.6-alkynyl, in particular C.sub.2-C.sub.4-alkynyl,
that is substituted by one, two or three or up to the maximum
possible number of identical or different groups R.sup.12a, as
defined and preferably defined herein.
[0080] According to a specific embodiment thereof, R.sup.2 is
C.sub.2-C.sub.6-haloalkynyl, in particular
C.sub.2-C.sub.4-haloalkynyl. According to a further specific
embodiment thereof, R.sup.2 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.6-alkynyl or
C.sub.3-C.sub.8-halocycloalkyl-C.sub.2-C.sub.6-alkynyl, in
particular C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.4-alkynyl or
C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.4-alkynyl. Specific
embodiments thereof can be found in the below Table P2.
[0081] According to still another embodiment, R.sup.2 is
phenyl-C.sub.1-C.sub.4-alkyl, in particular
phenyl-C.sub.1-C.sub.2-alkyl, such as benzyl, wherein the alkyl
moiety in each case is unsubstituted or carries one, two or three
R.sup.12a as defined and preferably defined herein, in particular
selected from halogen, in particular F and Cl,
C.sub.1-C.sub.4-alkoxy, in particular OCH.sub.3, and CN, and
wherein the phenyl in each case is unsubstituted or carries one,
two or three R.sup.12b as as defined and preferably defined herein,
in particular selected from halogen, in particular Cl and F,
C.sub.1-C.sub.4-alkoxy, in particular OCH.sub.3,
C.sub.1-C.sub.4-alkyl, in particular CH.sub.3 or C.sub.2H.sub.5,
and CN. Specific embodiments thereof can be found in the below
Table P2.
[0082] According to still another embodiment, R.sup.2 is
phenyl-C.sub.2-C.sub.4-alkenyl, in particular
phenyl-C.sub.2-C.sub.3-alkenyl, such as phenylethenyl, wherein the
alkenyl moiety in each case is unsubstituted or carries one, two or
three R.sup.12a as defined and preferably defined herein, in
particular selected from halogen, in particular F and Cl,
C.sub.1-C.sub.4-alkoxy, in particular OCH.sub.3, and CN, and
wherein the phenyl in each case is unsubstituted or carries one,
two or three R.sup.12b as defined and preferably defined herein, in
particular selected from halogen, in particular Cl and F,
C.sub.1-C.sub.4-alkoxy, in particular OCH.sub.3,
C.sub.1-C.sub.4-alkyl, in particular CH.sub.3 or C.sub.2H.sub.5,
and CN.
[0083] According to still another embodiment, R.sup.2 is
phenyl-C.sub.2-C.sub.4-alkynyl, in particular
phenyl-C.sub.2-C.sub.3-alkynyl, such as phenylethenyl, wherein the
alkynyl moiety in each case is unsubstituted or carries one, two or
three R.sup.12a, as defined and preferably defined herein, in
particular selected from halogen, in particular F and Cl,
C.sub.1-C.sub.4-alkoxy, in particular OCH.sub.3, and CN, and
wherein the phenyl in each case is unsubstituted or carries one,
two or three R.sup.12b as defined and preferably defined herein, in
particular selected from halogen, in particular Cl and F,
C.sub.1-C.sub.4-alkoxy, in particular OCH.sub.3,
C.sub.1-C.sub.4-alkyl, in particular CH.sub.3 or C.sub.2H.sub.5,
and CN.
[0084] According to still another embodiment, R.sup.2 is
C.sub.3-C.sub.8-cycloalkyl, in particular
C.sub.3-C.sub.6-cycloalkyl, such as C.sub.3H.sub.5 (cyclopropyl),
C.sub.4H.sub.7 (cyclobutyl), cyclopentyl or cyclohexyl. A further
embodiment relates to compounds, wherein R.sup.2 is
C.sub.3-C.sub.8-cycloalkyl, in particular
C.sub.3-C.sub.6-cycloalkyl, such as C.sub.3H.sub.5 (cyclopropyl) or
C.sub.4H.sub.7 (cyclobutyl), that is substituted by one, two, three
four or five or up to the maximum possible number of identical or
different groups R.sup.12b as defined and preferably defined
herein. According to a specific embodiment thereof, R.sup.2 is
C.sub.3-C.sub.8-halocycloalkyl, in particular
C.sub.3-C.sub.6-halocycloalkyl, such as halocyclopropyl, in
particular 1-F-cyclopropyl or 1-CIcyclopropyl. According to a
further specific embodiment thereof, R.sup.2 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.3-C.sub.8-cycloalkyl, in
particular C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-cycloalkyl,
wherein each of said cycloalkylcycloalkyl moieties is unsubstituted
or carries one, two or three R.sup.12b as defined and preferably
defined herein.
[0085] According to still another embodiment, R.sup.2 is phenyl,
wherein the phenyl is unsubstituted or carries one, two, three,
four or five independently selected R.sup.12b as defined and
preferably defined herein, in particular selected from halogen, in
particular Cl and F, C.sub.1-C.sub.4-alkoxy, in particular
OCH.sub.3, C.sub.1-C.sub.4-alkyl, in particular CH.sub.3 or
C.sub.2H.sub.5, and CN.
[0086] In a further embodiment of the invention, R.sup.2 is
selected from hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl and C.sub.2-C.sub.6-alkynyl, wherein the
R.sup.2 are in each case unsubstituted or are substituted by
R.sup.12a and/or R.sup.12b as defined and preferably defined
herein. In a specific embodiment thereof, R.sup.2 is selected from
hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl and
C.sub.2-C.sub.4-alkynyl, wherein the R.sup.2 are in each case
unsubstituted or are substituted by one, two or three R.sup.12a
and/or R.sup.12b as defined and preferably defined herein. In each
case, the substituents may also have the preferred meanings for the
respective substituent as defined above. Specific embodiments
thereof can be found in the below Table P2.
[0087] Particularly preferred embodiments of R.sup.2 according to
the invention are in Table P2 below, wherein each line of lines
P2-1 to P2-88 corresponds to one particular embodiment of the
invention, wherein P2-1 to P2-88 are also in any combination a
preferred embodiment of the present invention.
TABLE-US-00002 TABLE P2 line R.sup.2 P2-1 H P2-2 CH.sub.3 P2-3
CH.sub.2CH.sub.3 P2-4 CH(CH.sub.3).sub.2 P2-5
CH.sub.2CH.sub.2CH.sub.3 P2-6 CH.sub.2CH.sub.2CH.sub.2CH.sub.3 P2-7
CH.sub.2CH(CH.sub.3).sub.2 P2-8 CF.sub.3. P2-9 CHF.sub.2 P2-10
CFH.sub.2 P2-11 CCl.sub.3. P2-12 CHCl.sub.2 P2-13 CClH.sub.2 P2-14
CH.sub.2CF.sub.3 P2-15 CH.sub.2CHF.sub.2 P2-16 CH.sub.2CCl.sub.3
P2-17 CH.sub.2CHCl.sub.2 P2-18 CH.sub.2CH.sub.2OCH.sub.2CH.sub.3
P2-19 CH(CH.sub.3)OCH.sub.2CH.sub.3 P2-20 CH(CH.sub.3)OCH.sub.3
P2-21 CH.sub.2OCH.sub.3 P2-22 CH.sub.2CH.sub.2OCH.sub.3 P2-23
CH.sub.2OCF.sub.3 P2-24 CH.sub.2CH.sub.2OCF.sub.3 P2-25
CH.sub.2OCCl.sub.3 P2-26 CH.sub.2CH.sub.2OCCl.sub.3 P2-27
CH.sub.2CH.sub.2OH P2-28 CH.sub.2OH P2-29
CH.sub.2CH.sub.2CH.sub.2OH, P2-30 CH(CH.sub.3)CH.sub.2OH P2-31
CH.sub.2CH(CH.sub.3)OH P2-32 CH.sub.2CH.sub.2CH.sub.2CH.sub.2OH
P2-33 CH.sub.2CN, P2-34 CH.sub.2CH.sub.2CN, P2-35
CH.sub.2CH.sub.2CH.sub.2CN, P2-36 CH(CH.sub.3)CH.sub.2CN, P2-37
CH.sub.2CH(CH.sub.3)CN, P2-38 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN
P2-39 CH.dbd.CH.sub.2 P2-40 C(CH.sub.3).dbd.CH.sub.2 P2-41
CH.dbd.CHCH.sub.3 P2-42 CH.sub.2CH.dbd.CH.sub.2 P2-43
CH.sub.2CH.dbd.CHCH.sub.3 P2-44 CH.sub.2C(CH.sub.3).dbd.CH.sub.2
P2-45 C(CH.sub.3).dbd.CH(CH.sub.3) P2-46
C(CH.sub.3).dbd.C(CH.sub.3).sub.2 P2-47 CH.dbd.C(CH.sub.3).sub.2
P2-48 CH.dbd.C(Cl).sub.2 P2-49 C(CH.sub.3).dbd.CH.sub.2 P2-50
CH.sub.2C(Cl).dbd.CH.sub.2 P2-51 CH.sub.2C(H).dbd.CHCl P2-52
CH.dbd.CHCH.sub.2OH P2-53 CH.dbd.C(CH.sub.3)OH P2-54
CH.dbd.CHOCH.sub.3 P2-55 CH.dbd.CHCH.sub.2OCH.sub.3 P2-56
CH.sub.2CH.dbd.CHCH.sub.2OCH.sub.3 P2-57 CH.dbd.CHOCF.sub.3 P2-58
CH.dbd.CHCH.sub.2OCF.sub.3 P2-59 CH.dbd.CHOCCl.sub.3 P2-60
CH.dbd.CHCH.sub.2OCCl.sub.3 P2-61 CH.sub.2CH.dbd.CH(C.sub.3H.sub.5)
P2-62 CH.sub.2CH.dbd.CH(C.sub.4H.sub.7) P2-63
CH.sub.2CH.dbd.CH(1-Cl--C.sub.3H.sub.4) P2-64
CH.sub.2CH.dbd.CH(1-F--C.sub.3H.sub.4) P2-65 C.ident.CH P2-66
CH.sub.2C.ident.CH P2-67 CH.sub.2C.ident.CCH.sub.3 P2-68
CH.sub.2C.ident.CCH.sub.2CH.sub.3 P2-69 CH.sub.2C.ident.CCl P2-70
CH.sub.2C.ident.CF P2-71 CH.sub.2C.ident.C--I P2-72
CH.sub.2C.ident.CCH.sub.2OH P2-73 C.ident.COCH.sub.3 P2-74
CH.sub.2C.ident.COCH.sub.3 P2-75
CH.sub.2C.ident.CCCH.sub.2OCH.sub.3 P2-76 C.ident.COCF.sub.3 P2-77
CH.sub.2C.ident.COCF.sub.3 P2-78 C.ident.COCCl.sub.3 P2-79
CH.sub.2C.ident.COCCl.sub.3 P2-80 CH.sub.2-(cyclopropyl) P2-81
CH.sub.2-(cyclobutyl) P2-82 CH.sub.2-(1-Cl-cyclopropyl) P2-83
CH.sub.2-(1-F-cyclopropyl) P2-84 CH.sub.2C.sub.6H.sub.5 P2-85
CH.sub.2--(4-Cl)--C.sub.6H.sub.4 P2-86
CH.sub.2--(4-F)--C.sub.6H.sub.4 P2-87
CH.sub.2--(4-CH.sub.3)--C.sub.6H.sub.4 P2-88
CH.sub.2--(4-OCH.sub.3)--C.sub.6H.sub.4
[0088] Particularly preferred embodiments of combination of R.sup.1
and R.sup.2 according to the invention are given in Table A below,
wherein each line of lines A-1 to A-70 corresponds to one
particular embodiment of the invention, wherein A-1 to A-70 are
also in any combination a preferred embodiment for combinations of
R.sup.1 and R.sup.2 of the present invention.
[0089] R.sup.12a or more specifically, R.sup.12a1 are the possible
substituents for any aliphatic moiety of R.sup.1 and/or R.sup.2 and
can independently be defined for R.sup.1 and R.sup.2.
[0090] According to one embodiment, the respective R.sup.1 is not
further substituted. According to a further embodiment, the
respective R.sup.1 contains one, two, three or up to the maximum
possible number of identical or different groups R.sup.12a or
R.sup.12a1. According to still a further embodiment, the respective
R.sup.1 contains one, two or three identical or different groups
R.sup.12a or R.sup.12a1. According to one specific embodiment
thereof, the respective R.sup.1 contains one group R.sup.12a or
R.sup.12a1. According to one further specific embodiment thereof,
the respective R.sup.1 contains one or two identical or different
groups R.sup.12a or R.sup.12a1.
[0091] According to one embodiment, the respective R.sup.2 is not
further substituted. According to a further embodiment, the
respective R.sup.2 contains one, two, three or up to the maximum
possible number of identical or different groups R.sup.12a.
According to still a further embodiment, the respective R.sup.2
contains one, two or three identical or different groups R.sup.12a.
According to one specific embodiment thereof, the respective
R.sup.2 contains one group R.sup.12a. According to one further
specific embodiment thereof, the respective R.sup.2 contains one or
two identical or different groups R.sup.12a.
[0092] R.sup.12a according to the invention is independently
selected from halogen, OH, CN, nitro, C.sub.1-C.sub.4-alkoxy,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and
C.sub.1-C.sub.4-halogenalkoxy.
[0093] According to one embodiment R.sup.12a is independently
selected from halogen, OH, CN, C.sub.1-C.sub.2-alkoxy,
C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl and
C.sub.1-C.sub.2-halogenalkoxy. Specifically, R.sup.12a is
independently selected from F, Cl, OH, CN, C.sub.1-C.sub.2-alkoxy,
cyclopropyl, 1-F-cyclopropyl, 1-C.sub.1-cyclopropyl and
C.sub.1-C.sub.2-halogenalkoxy.
[0094] According to a further embodiment R.sup.12a is independently
selected from halogen, OH, CN, C.sub.3-C.sub.6-cycloalkyl and
C.sub.3-C.sub.6-halocycloalkyl. Specifically, R.sup.12a is
independently selected from F, Cl, OH, CN, cyclopropyl,
1-F-cyclopropyl and 1-C.sub.1-cyclopropyl.
[0095] R.sup.12a1 are independently of one another selected from
halogen, OH, CN, nitro, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl and C.sub.1-C.sub.4-halogenalkoxy,
in particular halogen, OH, CN, C.sub.3-C.sub.6-cycloalkyl and
C.sub.3-C.sub.8-halocycloalkyl. Specifically, R.sup.12a1 is
independently selected from F, Cl, OH, CN, cyclopropyl,
1-F-cyclopropyl and 1-C.sub.1-cyclopropyl.
R.sup.12b are the possible substituents for any cycloalkyl and/or
phenyl moiety of R.sup.1 and/or R.sup.2 and can independently be
defined for R.sup.1 and R.sup.2.
[0096] According to one embodiment, the respective R.sup.1 is not
further substituted. According to a further embodiment, the
respective R.sup.1 contains one, two, three or up to the maximum
possible number of identical or different groups R.sup.12b.
According to still a further embodiment, the respective R.sup.1
contains one, two or three identical or different groups R.sup.12b.
According to one specific embodiment thereof, the respective
R.sup.1 contains one group R.sup.12b. According to one further
specific embodiment thereof, the respective R.sup.1 contains one or
two identical or different groups Rub.
[0097] According to one embodiment, the respective R.sup.2 is not
further substituted. According to a further embodiment, the
respective R.sup.2 contains one, two, three or up to the maximum
possible number of identical or different groups R.sup.12b.
According to still a further embodiment, the respective R.sup.2
contains one, two or three identical or different groups R.sup.12b.
According to one specific embodiment thereof, the respective
R.sup.2 contains one group R.sup.12b. According to one further
specific embodiment thereof, the respective R.sup.2 contains one or
two identical or different groups R.sup.12b.
[0098] R.sup.12b according to the invention is is independently
selected from halogen, OH, CN, nitro, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and
C.sub.1-C.sub.4-halogenalkoxy.
[0099] According to one embodiment R.sup.12b is independently
selected from halogen, CN, nitro, C.sub.1-C.sub.2-alkyl,
C.sub.1-C.sub.2-alkoxy, C.sub.1-C.sub.2-halogenalkyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl and
C.sub.1-C.sub.2-halogenalkoxy. Specifically, R.sup.12b is
independently selected from F, Cl, OH, CN, nitro, CH.sub.3,
OCH.sub.3, cyclopropyl, 1-F-cyclopropyl, 1-C.sub.1-cyclopropyl and
halogenmethoxy.
[0100] R.sup.31 according to the invention is halogen.
[0101] According to one embodiment, R.sup.31 is F, corresponding to
compounds I.A:
##STR00019##
[0102] According to a further embodiment, R.sup.31 is Cl,
corresponding to compounds I.B:
##STR00020##
[0103] According to still a further embodiment, R.sup.31 is Br,
corresponding to compounds I.C:
##STR00021##
[0104] Each R.sup.4 according to the present invention is
independently selected from halogen, CN, NO.sub.2, OH, SH,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyloxy,
NH.sub.2, NH(C.sub.1-C.sub.4-alkyl),
N(C.sub.1-C.sub.4-alkyl).sub.2, NH(C.sub.3-C.sub.6-cycloalkyl),
N(C.sub.3-C.sub.6-cycloalkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)--(N(C.sub.3-C.sub.6-cycloalkyl).sub.2); wherein each of
R.sup.4 is unsubstituted or further substituted by one, two, three
or four R.sup.4a independently selected from halogen, CN, NO.sub.2,
OH, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl,
C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, with the
provisos given herein.
[0105] According to the invention, there can be zero, one, two,
three, four or five R.sup.4 present, namely for m is 0, 1, 2, 3, 4
or 5. In particular, m is 0, 1, 2, 3 or 4.
[0106] According to one embodiment, m is 0.
[0107] According to a further embodiment, m is 1, 2, 3 or 4, in
particular 1, 2 or 3, more specifically 1 or 2. According to one
specific embodiment thereof, m is 1, according to a further
specific embodiment, m is 2.
[0108] According to still a further embodiment, m is 2, 3 or 4.
[0109] According to still a further embodiment, m is 3.
[0110] According to one embodiment of the invention, one R.sup.4 is
attached to the para-position (4-position).
[0111] According to a further embodiment of the invention, one
R.sup.4 is attached to the meta-position (3-position).
[0112] According to a further embodiment of the invention, one
R.sup.4 is attached to the ortho-position (2-position).
[0113] According to a further embodiment of the invention, two
R.sup.4 are attached in 2,4-position.
[0114] According to a further embodiment of the invention, two
R.sup.4 are attached in 2,3-position.
[0115] According to a further embodiment of the invention, two
R.sup.4 are attached in 2,5-position.
[0116] According to a further embodiment of the invention, two
R.sup.4 are attached in 2,6-position.
[0117] According to a further embodiment of the invention, two
R.sup.4 are attached in 3,4-position.
[0118] According to a further embodiment of the invention, two
R.sup.4 are attached in 3,5-position.
[0119] According to a further embodiment of the invention, three
R.sup.4 are attached in 2,4,6-position.
[0120] According to one embodiment of the invention,
(R.sup.4).sub.m is selected from 2-(R.sup.4).sub.1,
3-(R.sup.4).sub.1, 2,3-(R.sup.4).sub.2, 2,5-(R.sup.4).sub.2,
2,6-(R.sup.4).sub.2, 3,4-(R.sup.4).sub.2, 3,5-(R.sup.4).sub.2,
2,3,4-(R.sup.4).sub.3, 2,3,5-(R.sup.4).sub.3, 2,3,6-(R.sup.4).sub.3
and 3,4,5- (R.sup.4).sub.3.
[0121] For every R.sup.4 that is present in the inventive
compounds, the following embodiments and preferences apply
independently of the meaning of any other R.sup.4 that may be
present in the phenyl ring. Furthermore, the particular embodiments
and preferences given herein for R.sup.4 apply independently for
each of m=1, m=2, m=3, m=4 and m=5, taking into account the
provisos according to the invention, however.
[0122] According to one embodiment, R.sup.4 is independently
selected from halogen, CN, NO.sub.2, OH, SH, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyloxy, NH.sub.2, NH(C.sub.1-C.sub.4-alkyl),
N(C.sub.1-C.sub.4-alkyl).sub.2, NH(C.sub.3-C.sub.6-cycloalkyl),
N(C.sub.3-C.sub.6-cycloalkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.4-alkyl) (p=0, 1 or 2),
C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)--(N(C.sub.3-C.sub.6-cycloalkyl).sub.2); wherein each of
R.sup.4 is unsubstituted or further substituted by one, two, three
or four independently selected R.sup.4a, wherein R.sup.4a is as
defined and preferably defined herein.
[0123] According to a further embodiment, R.sup.4 is independently
selected from halogen, CN, NO.sub.2, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.2-C.sub.4-alkenyl,
C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.3-C.sub.6-cycloalkyloxy, NH.sub.2,
NH(C.sub.1-C.sub.42-alkyl), N(C.sub.1-C.sub.2-alkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.2-alkyl) (p=0, 1 or 2),
C(.dbd.O)(C.sub.1-C.sub.2-alkyl), C(.dbd.O)(OH) and
C(.dbd.O)(O--C.sub.1-C.sub.2-alkyl), wherein each of R.sup.4 is
unsubstituted or further substituted by one, two, three or four
independently selected R.sup.4a, wherein R.sup.4a is as defined and
preferably defined herein.
[0124] According to a further embodiment, R.sup.4 is independently
selected from halogen, CN, NO.sub.2, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.4-alkenyl,
C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl,
C.sub.2-C.sub.4-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.3-C.sub.6-halocycloalkyl, S(C.sub.1-C.sub.2-alkyl),
S(O)(C.sub.1-C.sub.2-alkyl), S(O).sub.2(C.sub.1-C.sub.2-alkyl),
C(.dbd.O)(C.sub.1-C.sub.2-alkyl), C(.dbd.O)(OH) and
C(.dbd.O)(O--C.sub.1-C.sub.2-alkyl).
[0125] According to a further embodiment, R.sup.4 is independently
selected from halogen, CN, NO.sub.2, C.sub.1-C.sub.2-alkyl,
C.sub.1-C.sub.2-haloalkyl, C.sub.1-C.sub.2-alkoxy,
C.sub.1-C.sub.2-haloalkoxy, S(C.sub.1-C.sub.2-alkyl),
S(O)(C.sub.1-C.sub.2-alkyl), S(O).sub.2(C.sub.1-C.sub.2-alkyl),
C(.dbd.O)(OH) and C(.dbd.O)(O--C.sub.1-C.sub.2-alkyl).
[0126] According to a further embodiment, R.sup.4 is independently
selected from F, Cl, Br, CN, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, S(C.sub.1-C.sub.4-alkyl),
S(O)(C.sub.1-C.sub.4-alkyl) and
S(O).sub.2(C.sub.1-C.sub.4-alkyl).
[0127] According to still a further specific embodiment, R.sup.4 is
independently selected from CN, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and
C.sub.1-C.sub.4-haloalkoxy, in particular CN, CF.sub.3 and
OCF.sub.3.
[0128] According to still a further specific embodiment, R.sup.4 is
independently selected from halogen, in particular from Br, F. and
Cl, more specifically from F and C.sub.1.
[0129] According to a further specific embodiment, R.sup.4 is
CN.
[0130] According to one further embodiment R.sup.4 is NO.sub.2.
[0131] According to one further embodiment R.sup.4 is OH.
[0132] According to one further embodiment R.sup.4 is SH.
[0133] According to a further specific embodiment, R.sup.4 is
C.sub.1-C.sub.6-alkyl, in particular C.sub.1-C.sub.4-alkyl, such as
CH.sub.3. Further appropriate alkyls are ethyl, n-propyl, i-propyl,
n-butyl, i-butyl and t-butyl.
[0134] According to a further specific embodiment, R.sup.4 is
C.sub.1-C.sub.6-haloalkyl, in particular C.sub.1-C.sub.4-haloalkyl,
such as CF.sub.3, CHF.sub.2, CH.sub.2F, CCl.sub.3, CHCl.sub.2 or
CH.sub.2Cl.
[0135] According to a further specific embodiment R.sup.4 is
C.sub.1-C.sub.6-alkyl, preferably C.sub.1-C.sub.4-alkyl,
substituted by OH, more preferably CH.sub.2OH, CH.sub.2CH.sub.2OH,
CH.sub.2CH.sub.2CH.sub.2OH, CH(CH.sub.3)CH.sub.2OH,
CH.sub.2CH(CH.sub.3)OH, CH.sub.2CH.sub.2CH.sub.2CH.sub.2OH. In a
special embodiment R.sup.4 is CH.sub.2OH. According to a further
specific embodiment R.sup.4 is C.sub.1-C.sub.6-alkyl, preferably
C.sub.1-C.sub.4-alkyl substituted by CN, more preferably
CH.sub.2CN, CH.sub.2CH.sub.2CN, CH.sub.2CH.sub.2CH.sub.2CN,
CH(CH.sub.3)CH.sub.2CN, CH.sub.2CH(CH.sub.3)CN,
CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN. In a special embodiment R.sup.4
is CH.sub.2CH.sub.2CN. In a further special embodiment R.sup.4 is
CH(CH.sub.3)CN. According to a further specific embodiment R.sup.4
is C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl, more preferably
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl. In a special
embodiment R.sup.4 is CH.sub.2OCH.sub.3. In a further special
embodiment R.sup.4 is CH.sub.2CH.sub.2OCH.sub.3. In a further
special embodiment R.sup.4 is CH(CH.sub.3)OCH.sub.3. In a further
special embodiment R.sup.4 is CH(CH.sub.3)OCH.sub.2CH.sub.3. In a
further special embodiment R.sup.4 is
CH.sub.2CH.sub.2OCH.sub.2CH.sub.3. According to a further specific
embodiment R.sup.4 is
C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.6-alkyl, more preferably
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl. In a special
embodiment R.sup.4 is CH.sub.2OCF.sub.3. In a further special
embodiment R.sup.4 is CH.sub.2CH.sub.2OCF.sub.3. In a further
special embodiment R.sup.4 is CH.sub.2OCCl.sub.3. In a further
special embodiment R.sup.4 is CH.sub.2CH.sub.2OCCl.sub.3.
[0136] According to a further specific embodiment, R.sup.4 is
C.sub.1-C.sub.6-alkoxy, in particular C.sub.1-C.sub.4-alkoxy, more
specifically C.sub.1-C.sub.2-alkoxy such as OCH.sub.3 or
OCH.sub.2CH.sub.3.
[0137] According to a further specific embodiment, R.sup.4 is
C.sub.1-C.sub.6-haloalkoxy, in particular
C.sub.1-C.sub.4-haloalkoxy, more specifically
C.sub.1-C.sub.2-haloalkoxy such as OCF.sub.3, OCHF.sub.2,
OCH.sub.2F, OCCl.sub.3, OCHCl.sub.2 or OCH.sub.2Cl, in particular
OCF.sub.3, OCHF.sub.2, OCCl.sub.3 or OCHCl.sub.2.
[0138] According to still a further embodiment, R.sup.4 is
C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-haloalkenyl, in
particular C.sub.2-C.sub.4-alkenyl or C.sub.2-C.sub.4-haloalkenyl,
such as CH.dbd.CH.sub.2, CH.sub.2CH.dbd.CH.sub.2, CH.dbd.CHCH.sub.3
or C(CH.sub.3).dbd.CH.sub.2.
[0139] According to a further specific embodiment R.sup.4 is
C.sub.2-C.sub.6-alkenyl, preferably C.sub.2-C.sub.4-alkenyl,
substituted by OH, more preferably, CH.dbd.CHOH,
CH.dbd.CHCH.sub.2OH, C(CH.sub.3).dbd.CHOH, CH.dbd.C(CH.sub.3)OH. In
a special embodiment R.sup.4 is CH.dbd.CHOH. In a further special
embodiment R.sup.4 is CH.dbd.CHCH.sub.2OH. According to a further
specific embodiment R.sup.4 is
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.6-alkenyl, more preferably
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkenyl. In a special
embodiment R.sup.4 is CH.dbd.CHOCH.sub.3. In a further special
embodiment R.sup.4 is CH.dbd.CHCH.sub.2OCH.sub.3. According to a
further specific embodiment R.sup.4 is
C.sub.1-C.sub.4-haloalkoxy-C.sub.2-C.sub.6-alkenyl, more preferably
C.sub.1-C.sub.4-haloalkoxy-C.sub.2-C.sub.4-alkenyl. In a special
embodiment R.sup.4 is CH.dbd.CHOCF.sub.3. In a further special
embodiment R.sup.4 is CH.dbd.CHCH.sub.2OCF.sub.3. In a further
special embodiment R.sup.4 is CH.dbd.CHOCCl.sub.3. In a further
special embodiment R.sup.4 is CH.dbd.CHCH.sub.2OCCl.sub.3.
According to a further specific embodiment R.sup.4 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.6-alkenyl, preferably
C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.4-alkenyl. According to a
further specific embodiment R.sup.4 is
C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.4-alkenyl, preferably
C.sub.3-C.sub.8-halocycloalkyl-C.sub.2-C.sub.6-alkenyl.
[0140] According to still a further embodiment, R.sup.4 is
C.sub.2-C.sub.6-alkynyl or C.sub.2-C.sub.6-haloalkynyl, in
particular C.sub.2-C.sub.4-alkynyl or C.sub.2-C.sub.4-haloalkynyl,
such as C.ident.CH, CH.sub.2C.ident.CH or CH.sub.2CCCH.sub.3.
[0141] According to a further specific embodiment R.sup.4 is
C.sub.2-C.sub.6-alkynyl, preferably C.sub.2-C.sub.4-alkynyl,
substituted by OH, more preferably, CCOH, CH.sub.2CCOH. In a
special embodiment R.sup.4 is CCOH. In a further special embodiment
R.sup.4 is CH.sub.2CCOH. According to a further specific embodiment
R.sup.4 is C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.6-alkynyl, more
preferably C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkynyl. In a
special embodiment R.sup.4 is CCOCH.sub.3. In a further special
embodiment R.sup.4 is CH.sub.2CCOCH.sub.3. According to a further
specific embodiment R.sup.4 is
C.sub.1-C.sub.4-haloalkoxy-C.sub.2-C.sub.6-alkynyl, more preferably
C.sub.1-C.sub.4-haloalkoxy-C.sub.2-C.sub.4-alkynyl. In a special
embodiment R.sup.4 is CCOCF.sub.3. In a further special embodiment
R.sup.4 is CH.sub.2CCOCF.sub.3. In a further special embodiment
R.sup.4 is CCOCCl.sub.3. In a further special embodiment R.sup.4 is
CH.sub.2CCOCCl.sub.3. According to a further specific embodiment
R.sup.4 is C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.6-alkynyl,
preferably C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.4-alkynyl.
According to a further specific embodiment R.sup.4 is
C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.4-alkynyl, preferably
C.sub.3-C.sub.8-halocycloalkyl-C.sub.2-C.sub.6-alkynyl.
[0142] According to one another embodiment R.sup.4 is
C.sub.3-C.sub.8-cycloalkyl, preferably cyclopropyl, cyclobutyl,
cyclopentyl or cyclohexyl, in particular cyclopropyl or cyclobutyl.
In a special embodiment R.sup.4 is cyclopropyl. In a further
special embodiment R.sup.4 is cyclobutyl. In a further special
embodiment R.sup.4 is cyclopentyl. In a further special embodiment
R.sup.4 is cyclohexyl.
[0143] According to one another embodiment R.sup.4 is
C.sub.3-C.sub.8-cycloalkoxy, preferably
C.sub.3-C.sub.6-cycloalkoxy. In a special embodiment R.sup.4 is
O-cyclopropyl.
[0144] According to a specific embodiment R.sup.4 is
C.sub.3-C.sub.8-halocycloalkyl, more preferably fully or partially
halogenated C.sub.3-C.sub.6-cycloalkyl. In a special embodiment
R.sup.4 is fully or partially halogenated cyclopropyl. In a further
special embodiment R.sup.4 is 1-C.sub.1-cyclopropyl. In a further
special embodiment R.sup.4 is 2-C.sub.1-cyclopropyl. In a further
special embodiment R.sup.4 is 1-F-cyclopropyl. In a further special
embodiment R.sup.4 is 2-F-cyclopropyl. In a further special
embodiment R.sup.4 is fully or partially halogenated cyclobutyl. In
a further special embodiment R.sup.4 is 1-C.sub.1-cyclobutyl. In a
further special embodiment R.sup.4 is 1-F-cyclobutyl. In a further
special embodiment R.sup.4 is 3,3-Cl.sub.2-cyclobutyl. In a further
special embodiment R.sup.4 is 3,3-F2-cyclobutyl. According to a
specific embodiment R.sup.4 is C.sub.3-C.sub.8-cycloalkyl
substituted by C.sub.1-C.sub.4-alkyl, more preferably is
C.sub.3-C.sub.6-cycloalkyl substituted by C.sub.1-C.sub.4-alkyl. In
a special embodiment R.sup.4 is 1-CH.sub.3-cyclopropyl. According
to a specific embodiment R.sup.4 is C.sub.3-C.sub.8-cycloalkyl
substituted by CN, more preferably is C.sub.3-C.sub.6-cycloalkyl
substituted by CN. In a special embodiment R.sup.4 is
1-CN-cyclopropyl. According to a further specific embodiment
R.sup.4 is C.sub.3-C.sub.8-cycloalkyl-C.sub.3-C.sub.8-cycloalkyl,
preferably C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-cycloalkyl.
In a special embodiment R.sup.4 is cyclopropyl-cyclopropyl. In a
special embodiment R.sup.4 is 2-cyclopropyl-cyclopropyl.
[0145] According to a further specific embodiment R.sup.4 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.3-C.sub.8-halocycloalkyl,
preferably
C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-halocycloalkyl.
[0146] According to one another embodiment R.sup.4 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, preferably
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl. In a special
embodiment R.sup.4 is CH(CH.sub.3)(cyclopropyl). In a further
special embodiment R.sup.4 is CH.sub.2-(cyclopropyl).
[0147] According to a further preferred embodiment R.sup.4 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl wherein the alkyl
moiety can be substituted by one, two, three or up to the maximum
possible number of identical or different groups R.sup.a as defined
and preferably herein and the cycloalkyl moiety can be substituted
by one, two, three or up to the maximum possible number of
identical or different groups Rb as defined and preferably
herein.
[0148] According to a specific embodiment R.sup.4 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-haloalkyl,
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-haloalkyl. According to
a specific embodiment R.sup.4 is
C.sub.3-C.sub.8-halocycloalkyl-C.sub.1-C.sub.4-alkyl,
C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-Cealkyl. In a special
embodiment R.sup.4 is fully or partially halogenated
cyclopropyl-C.sub.1-C.sub.4-alkyl. In a further special embodiment
R.sup.4 is 1-C.sub.1-cyclopropyl-C.sub.1-C.sub.4-alkyl. In a
further special embodiment R.sup.4 is
1-F-cyclopropyl-C.sub.1-C.sub.4-alkyl.
[0149] According to one another embodiment R.sup.4 is NH.sub.2.
[0150] According to one another embodiment R.sup.4 is
NH(C.sub.1-C.sub.4-alkyl). According to a specific embodiment
R.sup.4 is NH(CH.sub.3). According to a specific embodiment R.sup.4
is NH(CH.sub.2CH.sub.3). According to a specific embodiment R.sup.4
is NH(CH.sub.2CH.sub.2CH.sub.3). According to a specific embodiment
R.sup.4 is NH(CH(CH.sub.3).sub.2). According to a specific
embodiment R.sup.4 is NH(CH.sub.2CH.sub.2CH.sub.2CH.sub.3).
According to a specific embodiment R.sup.4 is
NH(C(CH.sub.3).sub.3).
[0151] According to one another embodiment R.sup.4 is
N(C.sub.1-C.sub.4-alkyl).sub.2. According to a specific embodiment
R.sup.4 is N(CH.sub.3).sub.2. According to a specific embodiment
R.sup.4 is N(CH.sub.2CH.sub.3).sub.2. According to a specific
embodiment R.sup.4 is N(CH.sub.2CH.sub.2CH.sub.3).sub.2. According
to a specific embodiment R.sup.4 is
N(CH(CH.sub.3).sub.2).sub.2.
[0152] According to a specific embodiment R.sup.4 is
N(CH.sub.2CH.sub.2CH.sub.2CH.sub.3).sub.2. According to a specific
embodiment R.sup.4 is NH(C(CH.sub.3).sub.3).sub.2.
[0153] According to one another embodiment R.sup.4 is
NH(C.sub.3-C.sub.8-cycloalkyl) preferably
NH(C.sub.3-C.sub.6-cycloalkyl). According to a specific embodiment
R.sup.4 is NH(cyclopropyl). According to a specific embodiment
R.sup.4 is NH(cyclobutyl). According to a specific embodiment
R.sup.4 is NH(cyclopentyl). According to a specific embodiment
R.sup.4 is NH(cyclohexyl).
[0154] According to one another embodiment R.sup.4 is
N(C.sub.3-C.sub.8-cycloalkyl).sub.2 preferably
N(C.sub.3-C.sub.6-cycloalkyl).sub.2. According to a specific
embodiment R.sup.4 is N(cyclopropyl).sub.2. According to a specific
embodiment R.sup.4 is N(cyclobutyl).sub.2. According to a specific
embodiment R.sup.4 is N(cyclopentyl).sub.2. According to a specific
embodiment R.sup.4 is N(cyclohexyl).sub.2.
[0155] According to still a further embodiment, R.sup.4 is selected
from C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)(N(C.sub.3-C.sub.6-cycloalkyl).sub.2), in particular
selected from C(.dbd.O)(C.sub.1-C.sub.2-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.2-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.2-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.2-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)(N(C.sub.3-C.sub.6-cycloalkyl).sub.2). According to one
specific embodinvent thereof, R.sup.4 is C(.dbd.O)(OH) or
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl), in particular
C(.dbd.O)(OCH.sub.3).
[0156] According to one another embodiment R.sup.4 is
C(.dbd.O)(--C.sub.1-C.sub.4-alkyl). According to a specific
embodiment R.sup.4 is C(.dbd.O)CH.sub.3. According to a further
specific embodiment R.sup.4 is C(.dbd.O)CH.sub.2CH.sub.3. According
to a further specific embodiment R.sup.4 is
C(.dbd.O)CH.sub.2CH.sub.2CH.sub.3. According to a further specific
embodiment R.sup.4 is C(.dbd.O)CH(CH.sub.3).sub.2. According to a
further specific embodiment R.sup.4 is C(.dbd.O)C(CH.sub.3).sub.3.
BITTE ERGANZEN
[0157] According to one another embodiment R.sup.4 is
C(.dbd.O)OH.
[0158] According to one another embodiment R.sup.4 is
C(.dbd.O)(--O--C.sub.1-C.sub.4-alkyl). According to a specific
embodiment R.sup.4 is C(.dbd.O)OCH.sub.3. According to a further
specific embodiment R.sup.4 is C(.dbd.O)OCH.sub.2CH.sub.3.
According to a further specific embodiment R.sup.4 is
C(.dbd.O)OCH.sub.2CH.sub.2CH.sub.3. According to a further specific
embodiment R.sup.4 is C(.dbd.O)OCH(CH.sub.3).sub.2. According to a
further specific embodiment R.sup.4 is
C(.dbd.O)OC(CH.sub.3).sub.3.
[0159] According to one another embodiment R.sup.4 is
C(.dbd.O)--NH(C.sub.1-C.sub.4-alkyl). According to a specific
embodiment R.sup.4 is C(.dbd.O)NHCH.sub.3. According to a further
specific embodiment R.sup.4 is C(.dbd.O)NHCH.sub.2CH.sub.3.
According to a further specific embodiment R.sup.4 is
C(.dbd.O)NHCH.sub.2CH.sub.2CH.sub.3. According to a further
specific embodiment R.sup.4 is C(.dbd.O)NHCH(CH.sub.3).sub.2.
According to a further specific embodiment R.sup.4 is
C(.dbd.O)NHC(CH.sub.3).sub.3.
[0160] According to one another embodiment R.sup.4 is
C(.dbd.O)--N(C.sub.1-C.sub.4-alkyl).sub.2. According to a specific
embodiment R.sup.4 is C(.dbd.O)N(CH.sub.3).sub.2. According to a
further specific embodiment R.sup.4 is
C(.dbd.O)N(CH.sub.2CH.sub.3).sub.2. According to a further specific
embodiment R.sup.4 is C(.dbd.O)N(CH.sub.2CH.sub.2CH.sub.3).sub.2.
According to a further specific embodiment R.sup.4 is
C(.dbd.O)N(CH(CH.sub.3).sub.2).sub.2. According to a further
specific embodiment R.sup.4 is
C(.dbd.O)N(C(CH.sub.3).sub.3).sub.2.
[0161] According to one another embodiment R.sup.4 is
C(.dbd.O)--NH(C.sub.3-C.sub.6-cycloalkyl). According to a specific
embodiment R.sup.4 is C(.dbd.O)NH(cyclopropyl). According to a
further specific embodiment R.sup.4 is C(.dbd.O)NH(cyclobutyl).
According to a further specific embodiment R.sup.4 is
C(.dbd.O)NH(cyclopentyl). According to a further specific
embodiment R.sup.4 is C(.dbd.O)NH(cyclohexyl).
[0162] According to one another embodiment R.sup.4 is
C(.dbd.O)--N(C.sub.3-C.sub.6-cycloalkyl).sub.2. According to a
specific embodiment R.sup.4 is C(.dbd.O)N(cyclopropyl).sub.2.
According to a further specific embodiment R.sup.4 is
C(.dbd.O)N(cyclobutyl).sub.2. According to a further specific
embodiment R.sup.4 is C(.dbd.O)N(cyclopentyl).sub.2. According to a
further specific embodiment R.sup.4 is
C(.dbd.O)N(cyclohexyl).sub.2.
[0163] According to still a further embodiment, R.sup.4 is selected
from S(C.sub.1-C.sub.2-alkyl), S(O)(C.sub.1-C.sub.2-alkyl) and
S(O).sub.2(C.sub.1-C.sub.2-alkyl), in particular SCH.sub.3,
S(O)(CH.sub.3) and S(O).sub.2(CH.sub.3). According to a specific
embodiment R.sup.4 is selected from S(C.sub.1-C.sub.2-haloalkyl),
S(O)(C.sub.1-C.sub.2-haloalkyl) and
S(O).sub.2(C.sub.1-C.sub.2-haloalkyl), such as SO.sub.2CF.sub.3.
Particularly preferred embodiments of R.sup.4 according to the
invention are in Table P3 below, wherein each line of lines P3-1 to
P3-16 corresponds to one particular embodiment of the invention,
wherein P3-1 to P3-16 are also in any combination with one another
a preferred embodiment of the present invention. Thereby, for every
R.sup.4 that is present in the inventive compounds, these specific
embodiments and preferences apply independently of the meaning of
any other R.sup.4 that may be present in the phenyl ring:
TABLE-US-00003 TABLE P3 No. R.sup.4 P3-1 Cl P3-2 F P3-3 CN P3-4
NO.sub.2 P3-5 CH.sub.3 P3-6 CH.sub.2CH.sub.3 P3-7 CF.sub.3 P3-8
CHF.sub.2 P3-9 OCH.sub.3 P3-10 OCH.sub.2CH.sub.3 P3-11 OCF.sub.3
P3-12 OCHF.sub.2 P3-13 SCH.sub.3 P3-14 SOCH.sub.3 P3-15
SO.sub.2CH.sub.3 P3-16 CO.sub.2CH.sub.3
[0164] Particularly preferred embodiments of (R.sup.4).sub.m
according to the invention are in Table B below, wherein each line
of lines B-1 to B-153 corresponds to one particular embodiment of
the invention, wherein B-1 to B-153 are also in any combination a
preferred embodiment of the present invention, taking into account
the inventive provisos, where applicable. More particularly
preferred embodiments of (R.sup.4).sub.m according to the invention
are in Table B1 below, wherein each line of lines B1-1 to B1-64
corresponds to one particular embodiment of the invention, wherein
B1-1 to B1-64 are also in any combination a preferred embodiment of
the present invention, taking into account the inventive provisos,
where applicable.
TABLE-US-00004 TABLE B1 line (R.sup.4).sub.m B1-1 --* B1-2 2-Cl
B1-3 3-Cl B1-4 2-F B1-5 3-F B1-6 2-CN B1-7 3-CN B1-8 4-CN B1-9
2-NO.sub.2 B1-10 3-NO.sub.2 B1-11 4-NO.sub.2 B1-12 2-SCH.sub.3
B1-13 3-SCH.sub.3 B1-14 4-SCH.sub.3 B1-15 2-SOCH.sub.3 B1-16
3-SOCH.sub.3 B1-17 4-SOCH.sub.3 B1-18 2-SO.sub.2CH.sub.3 B1-19
3-SO.sub.2CH.sub.3 B1-20 4-SO.sub.2CH.sub.3 B1-21
2-CO.sub.2CH.sub.3 B1-22 3-CO.sub.2CH.sub.3 B1-23
4-CO.sub.2CH.sub.3 B1-24 2-CH.sub.3 B1-25 3-CH.sub.3 B1-26
4-CH.sub.3 B1-27 2-CF.sub.3 B1-28 3-CF.sub.3 B1-29 4-CF.sub.3 B1-30
2-CHF.sub.2 B1-31 3-CHF.sub.2 B1-32 4-CHF.sub.2 B1-33 2-OCH.sub.3
B1-34 3-OCH.sub.3 B1-35 4-OCH.sub.3 B1-36 2-OCF.sub.3 B1-37
3-OCF.sub.3 B1-38 4-OCF.sub.3 B1-39 2-OCHF.sub.2 B1-40 3-OCHF.sub.2
B1-41 4-OCHF.sub.2 B1-42 2,4,6-(CH.sub.3).sub.3 B1-43
2,4,6-(Cl).sub.3 B1-44 2,4,6-(F).sub.3 B1-45 2,3-Cl.sub.2 B1-46
2,4-Cl.sub.2 B1-47 2,5-Cl.sub.2 B1-48 3,4-Cl.sub.2 B1-49
3,5-Cl.sub.2 B1-50 2,6-Cl.sub.2 B1-51 2,3-F.sub.2 B1-52 2,4-F.sub.2
B1-53 2,5-F.sub.2 B1-54 3,4-F.sub.2 B1-55 3,5-F.sub.2 B1-56
2,6-F.sub.2 B1-57 2-CF.sub.3-4-Cl B1-58 2-CF.sub.3-4-F B1-59
2-Cl-4-CF.sub.3 B1-60 2-F-4-CF.sub.3 B1-61 2-CN-4-Cl B1-62 2-CN-4-F
B1-63 2-Cl-4-CN B1-64 2-F-4-CN
[0165] According to the invention, the following provisos
apply:
if m=1, R.sup.4 is not para-halogen; if R.sup.31 is Cl and m=2,
(R.sup.4).sub.m is not 2,4-di-halogen, wherein each halogen is
selected from Cl and F; and if R.sup.31 is Cl and m=3,
(R.sup.4).sub.m is not 2,4,6-tri-halogen, wherein each halogen is
selected from Cl and F, wherein these provisos refer to any
embodiment, where applicable.
[0166] In a particular embodiment, the provisos are as follows:
with the proviso that if m=1, R.sup.4 is not para-halogen; with the
proviso that if R.sup.31 is Cl and m=2, (R.sup.4).sub.m is not
2,4-di-halogen; and with the proviso that if R.sup.31 is Cl and
m=3, (R.sup.4).sub.m is not 2,4,6-tri-halogen;
[0167] According to a more particular embodiment, the provisos are
as follows:
if m=1, R.sup.4 is not para-halogen; if m=2, (R.sup.4).sub.m is not
2,4-di-halogen; and if m=3, (R.sup.4).sub.m is not
2,4,6-tri-halogen; wherein these provisos refer to any embodiment,
where applicable.
[0168] According to one embodiment, m is 1, 2, 3, 4 or 5 and one of
the R.sup.4 is independently selected from CN, NO.sub.2, OH, SH,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyloxy,
NH.sub.2, NH(C.sub.1-C.sub.4-alkyl),
N(C.sub.1-C.sub.4-alkyl).sub.2, NH(C.sub.3-C.sub.6-cycloalkyl),
N(C.sub.3-C.sub.6-cycloalkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)(N(C.sub.3-C.sub.6-cycloalkyl).sub.2; wherein each of
R.sup.4 is unsubstituted or further substituted by one, two, three
or four R.sup.4a as defined and preferably defined herein, wherein
said R.sup.4 may also be one of the preferred substituents as
defined herein comprising these substituents. The other R.sup.4, if
present, are independently selected from halogen, in particular Cl,
Br or F, and the other substituents as defined and preferably
defined for R.sup.4 herein.
[0169] According to one specific embodiment of the invention, m is
1 and R.sup.4 is in ortho- or meta-position.
[0170] According to one specific embodiment of the invention, m is
2, 3 or 4 and two of the R.sup.4 are in 2,3-, 3,4-, 3,5- or
2,6-position.
[0171] According to one specific embodiment, the present invention
relates to the following compounds Ia:
##STR00022##
wherein R.sup.43 is selected from CN, NO.sub.2, OH, SH,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl and
C.sub.3-C.sub.8-cycloalkyloxy, in particular selected from CN,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy and C.sub.1-C.sub.6-haloalkoxy.
[0172] According to a further specific embodiment, m is 2, 3 or 4
and two of the R.sup.4 are in 2,4-position, wherein one (called
R.sup.4-1) of said two substituents is selected from CN, NO.sub.2,
OH, SH, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyloxy,
NH.sub.2, NH(C.sub.1-C.sub.4-alkyl),
N(C.sub.1-C.sub.4-alkyl).sub.2, NH(C.sub.3-C.sub.6-cycloalkyl),
N(C.sub.3-C.sub.6-cycloalkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)--(N(C.sub.3-C.sub.6-cycloalkyl).sub.2; wherein each
substituent is unsubstituted or further substituted by one, two,
three or four R.sup.4a as defined and preferably defined herein;
and wherein the other one (called R.sup.4-2) is halogen or selected
from the substituents as defined for R.sup.4-1.
[0173] According to still a further specific embodiment, m is 2, 3
or 4 and the compounds have the following formula I.2a:
##STR00023##
wherein [0174] R.sup.45' is selected from CN, NO.sub.2, OH, SH,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyloxy,
NH.sub.2, NH(C.sub.1-C.sub.4-alkyl),
N(C.sub.1-C.sub.4-alkyl).sub.2, NH(C.sub.3-C.sub.6-cycloalkyl),
N(C.sub.3-C.sub.6-cycloalkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)--(N(C.sub.3-C.sub.6-cycloalkyl).sub.2; wherein each of
R.sup.45' is unsubstituted or further substituted by one, two,
three or four R.sup.45'a; wherein [0175] R.sup.45'a is
independently selected from halogen, CN, NO.sub.2, OH,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl,
C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; [0176]
R.sup.43' is halogen or selected from the substituents as defined
for R.sup.45'; wherein said R.sup.43' are unsubstituted or further
substituted by one, two, three or four R.sup.43'a, wherein each
R.sup.43'a is independently selected from the substituents as
defined for R.sup.45'a; [0177] o is 0, 1 or 2; [0178] R.sup.4 is as
defined and preferably defined herein.
[0179] According to still a further specific embodiment, in the
compounds of formula I.2a, o is 0, R.sup.45'' is halogen and
R.sup.43'' is selected from CN, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy,
S(C.sub.1-C.sub.4-alkyl), S(O)(C.sub.1-C.sub.4-alkyl) or
S(O.sub.2)(C.sub.1-C.sub.4-alkyl).
[0180] According to still a further specific embodiment, m is 2, 3
or 4 and the compounds have the formula I.2b
##STR00024##
wherein [0181] R.sup.43'' is selected from CN, NO.sub.2, OH, SH,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyloxy,
NH.sub.2, NH(C.sub.1-C.sub.4-alkyl),
N(C.sub.1-C.sub.4-alkyl).sub.2, NH(C.sub.3-C.sub.6-cycloalkyl),
N(C.sub.3-C.sub.6-cycloalkyl).sub.2,
S(O).sub.p(C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(C.sub.1-C.sub.4-alkyl), C(.dbd.O)(OH),
C(.dbd.O)(O--C.sub.1-C.sub.4-alkyl),
C(.dbd.O)(NH(C.sub.1-C.sub.4-alkyl)),
C(.dbd.O)(N(C.sub.1-C.sub.4-alkyl).sub.2),
C(.dbd.O)(NH(C.sub.3-C.sub.6-cycloalkyl)) and
C(.dbd.O)--(N(C.sub.3-C.sub.6-cycloalkyl).sub.2; wherein each of
R.sup.43'' is unsubstituted or further substituted by one, two,
three or four R.sup.43''a; wherein [0182] R.sup.43''a is
independently selected from halogen, CN, NO.sub.2, OH,
C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.4-alkoxy and
C.sub.1-C.sub.4-haloalkoxy; [0183] R.sup.45'' is halogen or
selected from the substituents as defined for R.sup.43''; wherein
said R.sup.45'' are unsubstituted or further substituted by one,
two, three or four R.sup.45''a, wherein each R.sup.45''a is
independently selected from the substituents as defined for
R.sup.43''a; [0184] o is 0, 1 or 2; [0185] R.sup.4 is as defined
and preferably defined herein.
[0186] In particular with a view to their use, preference is given
to the compounds of the formula I, in particular I.A, I.B and I.C,
compiled in the Tables 1a to 70a, Tables 1 b to 70b and Tables 1c
to 70c below, taking into account the inventive provisos, where
applicable. Each of the groups mentioned for a substituent in the
tables is furthermore per se, independently of the combination in
which it is mentioned, a particularly preferred aspect of the
substituent in question.
[0187] Table 1a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-1 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds I.A.M.B1
to I.A.M.B153).
[0188] Table 2a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-2 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.A.A2.B1 to I.A.A2.B153).
[0189] Table 3a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-3 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.A.A3.B1 to I.A.A3.B153).
[0190] Table 4a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-4 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.A.A4.B1 to I.A.A4.B153).
[0191] Table 5a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-5 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.A.A5.B1 to I.A.A5.B153).
[0192] Table 6a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-6 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.A.A6.B1 to I.A.A6.B153).
[0193] Table 7a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-7 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.A.A7.B1 to I.A.A7.B153).
[0194] Table 8a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-8 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.A.A8.B1 to I.A.A8.B153).
[0195] Table 9a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-9 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.A.A9.B1 to I.A.A9.B153).
[0196] Table 10a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-10 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A10.B1 to I.A.A10.B153).
[0197] Table 11a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-11 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A11.B1 to I.A.A11.B153).
[0198] Table 12a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-12 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A12.B1 to I.A.A12.B153).
[0199] Table 13a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-13 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A13.B1 to I.A.A13.B153).
[0200] Table 14a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-14 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A14.B1 to I.A.A14.B153).
[0201] Table 15a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-15 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A15.B1 to I.A.A15.B153).
[0202] Table 16a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-16 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A16.B1 to I.A.A16.B153).
[0203] Table 17a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-17 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A17.B1 to I.A.A17.B153).
[0204] Table 18a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-18 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A18.B1 to I.A.A18.B153).
[0205] Table 19a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-19 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A19.B1 to I.A.A19.B153).
[0206] Table 20a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-20 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A20.B1 to I.A.A20.B153).
[0207] Table 21a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-21 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A21.B1 to I.A.A21.B153).
[0208] Table 22a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-22 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A22.B1 to I.A.A22.B153).
[0209] Table 23a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-23 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A23.B1 to I.A.A23.B153).
[0210] Table 24a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-24 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A24.B1 to I.A.A24.B153).
[0211] Table 25a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-25 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A25.B1 to I.A.A25.B153).
[0212] Table 26a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-26 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A26.B1 to I.A.A26.B153).
[0213] Table 27a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-27 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A27.B1 to I.A.A27.B153).
[0214] Table 28a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-28 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A28.B1 to I.A.A28.B153).
[0215] Table 29a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-29 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A29.B1 to I.A.A29.B153).
[0216] Table 30a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-30 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A30.B1 to I.A.A30.B153).
[0217] Table 31a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-31 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A31.B1 to I.A.A31.B153).
[0218] Table 32a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-32 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A32.B1 to I.A.A32.B153).
[0219] Table 33a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-33 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A33.B1 to I.A.A33.B153).
[0220] Table 34a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-34 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A34.B1 to I.A.A34.B153).
[0221] Table 35a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-35 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A35.B1 to I.A.A35.B153).
[0222] Table 36a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-36 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A36.B1 to I.A.A36.B153).
[0223] Table 37a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-37 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A37.B1 to I.A.A37.B153).
[0224] Table 38a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-38 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A38.B1 to I.A.A38.B153).
[0225] Table 39a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-39 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A39.B1 to I.A.A39.B153).
[0226] Table 40a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-40 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A40.B1 to I.A.A40.B153).
[0227] Table 41a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-41 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A41.B1 to I.A.A41.B153).
[0228] Table 42a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-42 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A42.B1 to I.A.A42.B153).
[0229] Table 43a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-43 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A43.B1 to I.A.A43.B153).
[0230] Table 44a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-44 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A44.B1 to I.A.A44.B153).
[0231] Table 45a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-45 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A45.B1 to I.A.A45.B153).
[0232] Table 46a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-46 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A46.B1 to I.A.A46.B153).
[0233] Table 47a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-47 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A47.B1 to I.A.A47.B153).
[0234] Table 48a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-48 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A48.B1 to I.A.A48.B153).
[0235] Table 49a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-49 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A49.B1 to I.A.A49.B153).
[0236] Table 50a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-50 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A50.B1 to I.A.A50.B153).
[0237] Table 51a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-51 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A51.B1 to I.A.A51.B153).
[0238] Table 52a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-52 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A52.B1 to I.A.A52.B153).
[0239] Table 53a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-53 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A53.B1 to I.A.A53.B153).
[0240] Table 54a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-54 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A54.B1 to I.A.A54.B153).
[0241] Table 55a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-55 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A55.B1 to I.A.A55.B153).
[0242] Table 56a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-56 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A56.B1 to I.A.A56.B153).
[0243] Table 57a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-57 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A57.B1 to I.A.A57.B153).
[0244] Table 58a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-58 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A58.B1 to I.A.A58.B153).
[0245] Table 59a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-59 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A59.B1 to I.A.A59.B153).
[0246] Table 60a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-60 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A60.B1 to I.A.A60.B153).
[0247] Table 61a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-61 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A61.B1 to I.A.A61.B153).
[0248] Table 62a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-62 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A62.B1 to I.A.A62.B153).
[0249] Table 63a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-63 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A63.B1 to I.A.A63.B153).
[0250] Table 64a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-64 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A64.B1 to I.A.A64.B153).
[0251] Table 65a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-65 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A65.B1 to I.A.A65.B153).
[0252] Table 66a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-66 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A66.B1 to I.A.A66.B153).
[0253] Table 67a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-67 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A67.B1 to I.A.A67.B153).
[0254] Table 68a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-68 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A68.B1 to I.A.A68.B153).
[0255] Table 69a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-69 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A69.B1 to I.A.A69.B153).
[0256] Table 70a Compounds of the formula I.A in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-70 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.A.A70.B1 to I.A.A70.B153).
[0257] Table 1b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-1 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.B.A1.B1 to I.B.A1.B153).
[0258] Table 2b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-2 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.B.A2.B1 to I.B.A2.B153).
[0259] Table 3b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-3 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.B.A3.B1 to I.B.A3.B153).
[0260] Table 4b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-4 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.B.A4.B1 to I.B.A4.B153).
[0261] Table 5b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-5 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.B.A5.B1 to I.B.A5.B153).
[0262] Table 6b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-6 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.B.A6.B1 to I.B.A6.B153).
[0263] Table 7b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-7 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.B.A7.B1 to I.B.A7.B153).
[0264] Table 8b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-8 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.B.A8.B1 to I.B.A8.B153).
[0265] Table 9b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-9 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.B.A9.B1 to I.B.A9.B153).
[0266] Table 10b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-10 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A10.B1 to I.B.A10.B153).
[0267] Table 11b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-11 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A11.B1 to I.B.A11.B153).
[0268] Table 12b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-12 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A12.B1 to I.B.A12.B153).
[0269] Table 13b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-13 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A13.B1 to I.B.A13.B153).
[0270] Table 14b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-14 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A14.B1 to I.B.A14.B153).
[0271] Table 15b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-15 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A15.B1 to I.B.A15.B153).
[0272] Table 16b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-16 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A16.B1 to I.B.A16.B153).
[0273] Table 17b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-17 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A17.B1 to I.B.A17.B153).
[0274] Table 18b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-18 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A18.B1 to I.B.A18.B153).
[0275] Table 19b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-19 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A19.B1 to I.B.A19.B153).
[0276] Table 20b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-20 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A20.B1 to I.B.A20.B153).
[0277] Table 21 b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-21 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A21.B1 to I.B.A21.B153).
[0278] Table 22b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-22 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A22.B1 to I.B.A22.B153).
[0279] Table 23b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-23 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A23.B1 to I.B.A23.B153).
[0280] Table 24b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-24 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A24.B1 to I.B.A24.B153).
[0281] Table 25b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-25 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A25.B1 to I.B.A25.B153).
[0282] Table 26b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-26 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A26.B1 to I.B.A26.B153).
[0283] Table 27b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-27 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A27.B1 to I.B.A27.B153).
[0284] Table 28b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-28 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A28.B1 to I.B.A28.B153).
[0285] Table 29b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-29 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A29.B1 to I.B.A29.B153).
[0286] Table 30b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-30 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A30.B1 to I.B.A30.B153).
[0287] Table 31 b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-31 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A31.B1 to I.B.A31.B153).
[0288] Table 32b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-32 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A32.B1 to I.B.A32.B153).
[0289] Table 33b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-33 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A33.B1 to I.B.A33.B153).
[0290] Table 34b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-34 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A34.B1 to I.B.A34.B153).
[0291] Table 35b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-35 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A35.B1 to I.B.A35.B153).
[0292] Table 36b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-36 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A36.B1 to I.B.A36.B153).
[0293] Table 37b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-37 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A37.B1 to I.B.A37.B153).
[0294] Table 38b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-38 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A38.B1 to I.B.A38.B153).
[0295] Table 39b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-39 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A39.B1 to I.B.A39.B153).
[0296] Table 40b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-40 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A40.B1 to I.B.A40.B153).
[0297] Table 41 b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-41 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A41.B1 to I.B.A41.B153).
[0298] Table 42b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-42 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A42.B1 to I.B.A42.B153).
[0299] Table 43b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-43 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A43.B1 to I.B.A43.B153).
[0300] Table 44b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-44 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A44.B1 to I.B.A44.B153).
[0301] Table 45b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-45 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A45.B1 to I.B.A45.B153).
[0302] Table 46b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-46 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A46.B1 to I.B.A46.B153).
[0303] Table 47b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-47 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A47.B1 to I.B.A47.B153).
[0304] Table 48b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-48 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A48.B1 to I.B.A48.B153).
[0305] Table 49b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-49 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A49.B1 to I.B.A49.B153).
[0306] Table 50b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-50 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A50.B1 to I.B.A50.B153).
[0307] Table 51b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-51 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A51.B1 to I.B.A51.B153).
[0308] Table 52b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-52 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A52.B1 to I.B.A52.B153).
[0309] Table 53b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-53 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A53.B1 to I.B.A53.B153).
[0310] Table 54b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-54 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A54.B1 to I.B.A54.B153).
[0311] Table 55b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-55 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A55.B1 to I.B.A55.B153).
[0312] Table 56b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-56 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A56.B1 to I.B.A56.B153).
[0313] Table 57b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-57 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A57.B1 to I.B.A57.B153).
[0314] Table 58b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-58 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A58.B1 to I.B.A58.B153).
[0315] Table 59b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-59 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A59.B1 to I.B.A59.B153).
[0316] Table 60b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-60 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A60.B1 to I.B.A60.B153).
[0317] Table 61 b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-61 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A61.B1 to I.B.A61.B153).
[0318] Table 62b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-62 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A62.B1 to I.B.A62.B153).
[0319] Table 63b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-63 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A63.B1 to I.B.A63.B153).
[0320] Table 64b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-64 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A64.B1 to I.B.A64.B153).
[0321] Table 65b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-65 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A65.B1 to I.B.A65.B153).
[0322] Table 66b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-66 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A66.B1 to I.B.A66.B153).
[0323] Table 67b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-67 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A67.B1 to I.B.A67.B153).
[0324] Table 68b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-68 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A68.B1 to I.B.A68.B153).
[0325] Table 69b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-69 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A69.B1 to I.B.A69.B153).
[0326] Table 70b Compounds of the formula I.B in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-70 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.B.A70.B1 to I.B.A70.B153).
[0327] Table 1c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-1 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.C.A1.B1 to I.C.A1.B153).
[0328] Table 2c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-2 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.C.A2.B1 to I.C.A2.B153).
[0329] Table 3c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-3 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.C.A3.B1 to I.C.A3.B153).
[0330] Table 4c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-4 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.C.A4.B1 to I.C.A4.B153).
[0331] Table 5c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-5 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.C.A5.B1 to I.C.A5.B153).
[0332] Table 6c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-6 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.C.A6.B1 to I.C.A6.B153).
[0333] Table 7c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-7 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.C.A7.B1 to I.C.A7.B153).
[0334] Table 8c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-8 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.C.A8.B1 to I.C.A8.B153).
[0335] Table 9c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-9 of Table
A and the meaning for (R.sup.4).sub.m for each individual compound
corresponds in each case to one line of Table B (compounds
I.C.A9.B1 to I.C.A9.B153).
[0336] Table 10c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-10 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A10.B1 to I.C.A10.B153).
[0337] Table 11c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-11 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A11.B1 to I.C.A11.B153).
[0338] Table 12c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-12 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A12.B1 to I.C.A12.B153).
[0339] Table 13c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-13 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A13.B1 to I.C.A13.B153).
[0340] Table 14c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-14 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A14.B1 to I.C.A14.B153).
[0341] Table 15c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-15 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A15.B1 to I.C.A15.B153).
[0342] Table 16c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-16 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A16.B1 to I.C.A16.B153).
[0343] Table 17c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-17 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A17.B1 to I.C.A17.B153).
[0344] Table 18c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-18 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A18.B1 to I.C.A18.B153).
[0345] Table 19c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-19 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A19.B1 to I.C.A19.B153).
[0346] Table 20c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-20 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A20.B1 to I.C.A20.B153).
[0347] Table 21c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-21 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A21.B1 to I.C.A21.B153).
[0348] Table 22c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-22 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A22.B1 to I.C.A22.B153).
[0349] Table 23c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-23 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A23.B1 to I.C.A23.B153).
[0350] Table 24c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-24 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A24.B1 to I.C.A24.B153).
[0351] Table 25c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-25 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A25.B1 to I.C.A25.B153).
[0352] Table 26c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-26 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A26.B1 to I.C.A26.B153).
[0353] Table 27c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-27 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A27.B1 to I.C.A27.B153).
[0354] Table 28c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-28 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A28.B1 to I.C.A28.B153).
[0355] Table 29c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-29 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A29.B1 to I.C.A29.B153).
[0356] Table 30c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-30 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A30.B1 to I.C.A30.B153).
[0357] Table 31c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-31 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A31.B1 to I.C.A31.B153).
[0358] Table 32c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-32 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A32.B1 to I.C.A32.B153).
[0359] Table 33c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-33 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A33.B1 to I.C.A33.B153).
[0360] Table 34c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-34 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A34.B1 to I.C.A34.B153).
[0361] Table 35c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-35 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A35.B1 to I.C.A35.B153).
[0362] Table 36c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-36 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A36.B1 to I.C.A36.B153).
[0363] Table 37c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-37 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A37.B1 to I.C.A37.B153).
[0364] Table 38c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-38 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A38.B1 to I.C.A38.B153).
[0365] Table 39c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-39 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A39.B1 to I.C.A39.B153).
[0366] Table 40c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-40 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A40.B1 to I.C.A40.B153).
[0367] Table 41c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-41 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A41.B1 to I.C.A41.B153).
[0368] Table 42c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-42 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A42.B1 to I.C.A42.B153).
[0369] Table 43c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-43 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A43.B1 to I.C.A43.B153).
[0370] Table 44c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-44 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A44.B1 to I.C.A44.B153).
[0371] Table 45c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-45 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A45.B1 to I.C.A45.B153).
[0372] Table 46c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-46 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A46.B1 to I.C.A46.B153).
[0373] Table 47c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-47 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A47.B1 to I.C.A47.B153).
[0374] Table 48c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-48 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A48.B1 to I.C.A48.B153).
[0375] Table 49c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-49 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A49.B1 to I.C.A49.B153).
[0376] Table 50c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-50 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A50.B1 to I.C.A50.B153).
[0377] Table 51c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-51 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A51.B1 to I.C.A51.B153).
[0378] Table 52c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-52 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A52.B1 to I.C.A52.B153).
[0379] Table 53c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-53 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A53.B1 to I.C.A53.B153).
[0380] Table 54c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-54 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A54.B1 to I.C.A54.B153).
[0381] Table 55c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-55 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A55.B1 to I.C.A55.B153).
[0382] Table 56c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-56 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A56.B1 to I.C.A56.B153).
[0383] Table 57c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-57 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A57.B1 to I.C.A57.B153).
[0384] Table 58c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-58 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A58.B1 to I.C.A58.B153).
[0385] Table 59c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-59 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A59.B1 to I.C.A59.B153).
[0386] Table 60c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-60 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A60.B1 to I.C.A60.B153).
[0387] Table 61c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-61 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A61.B1 to I.C.A61.B153).
[0388] Table 62c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-62 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A62.B1 to I.C.A62.B153).
[0389] Table 63c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-63 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A63.B1 to I.C.A63.B153).
[0390] Table 64c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-64 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A64.B1 to I.C.A64.B153).
[0391] Table 65c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-65 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A65.B1 to I.C.A65.B153).
[0392] Table 66c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-66 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A66.B1 to I.C.A66.B153).
[0393] Table 67c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-67 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A67.B1 to I.C.A67.B153).
[0394] Table 68c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-68 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A68.B1 to I.C.A68.B153).
[0395] Table 69c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-69 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A69.B1 to I.C.A69.B153).
[0396] Table 70c Compounds of the formula I.C in which the
combination of R.sup.1 and R.sup.2 corresponds to line A-70 of
Table A and the meaning for (R.sup.4).sub.m for each individual
compound corresponds in each case to one line of Table B (compounds
I.C.A70.B1 to I.C.A70.B153).
TABLE-US-00005 TABLE A line R.sup.1 R.sup.2 A-1 H H A-2 CH.sub.3 H
A-3 CH.sub.2CH.sub.3 H A-4 CH(CH.sub.3).sub.2 H A-5 C.sub.3H.sub.5
H (cyclopropyl) A-6 C.sub.4H.sub.7 (cyclobutyl) H A-7
C.ident.CCH.sub.3 H A-8 C(CH.sub.3).sub.3 H A-9 CF.sub.3 H A-10
CHF.sub.2 H A-11 CH.dbd.CHCH.sub.3 H A-12 C(CH.sub.3).dbd.CH.sub.2
H A-13 1-(Cl)-cyclopropyl H A-14 1-(F)-cyclopropyl H A-15 H
CH.sub.3 A-16 CH.sub.3 CH.sub.3 A-17 CH.sub.2CH.sub.3 CH.sub.3 A-18
CH(CH.sub.3).sub.2 CH.sub.3 A-19 C.sub.3H.sub.5 CH.sub.3
(cyclopropyl) A-20 C.sub.4H.sub.7 (cyclobutyl) CH.sub.3 A-21
C.ident.CCH.sub.3 CH.sub.3 A-22 C(CH.sub.3).sub.3 CH.sub.3 A-23
CF.sub.3 CH.sub.3 A-24 CHF.sub.2 CH.sub.3 A-25 CH.dbd.CHCH.sub.3
CH.sub.3 A-26 C(CH.sub.3).dbd.CH.sub.2 CH.sub.3 A-27
1-(Cl)-cyclopropyl CH.sub.3 A-28 1-(F)-cyclopropyl CH.sub.3 A-29 H
CH.sub.2CH.sub.3 A-30 CH.sub.3 CH.sub.2CH.sub.3 A-31
CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 A-32 CH(CH.sub.3).sub.2
CH.sub.2CH.sub.3 A-33 C.sub.3H.sub.5 CH.sub.2CH.sub.3 (cyclopropyl)
A-34 C.sub.4H.sub.7 (cyclobutyl) CH.sub.2CH.sub.3 A-35
C.ident.CCH.sub.3 CH.sub.2CH.sub.3 A-36 C(CH.sub.3).sub.3
CH.sub.2CH.sub.3 A-37 CF.sub.3 CH.sub.2CH.sub.3 A-38 CHF.sub.2
CH.sub.2CH.sub.3 A-39 CH.dbd.CHCH.sub.3 CH.sub.2CH.sub.3 A-40
C(CH.sub.3).dbd.CH.sub.2 CH.sub.2CH.sub.3 A-41 1-(Cl)-cyclopropyl
CH.sub.2CH.sub.3 A-42 1-(F)-cyclopropyl CH.sub.2CH.sub.3 A-43 H
CH.sub.2--CH.dbd.CH.sub.2 A-44 CH.sub.3 CH.sub.2--CH.dbd.CH.sub.2
A-45 CH.sub.2CH.sub.3 CH.sub.2--CH.dbd.CH.sub.2 A-46
CH(CH.sub.3).sub.2 CH.sub.2--CH.dbd.CH.sub.2 A-47 C.sub.3H.sub.5
CH.sub.2--CH.dbd.CH.sub.2 (cyclopropyl) A-48 C.sub.4H.sub.7
(cyclobutyl) CH.sub.2--CH.dbd.CH.sub.2 A-49 C.ident.CCH.sub.3
CH.sub.2--CH.dbd.CH.sub.2 A-50 C(CH.sub.3).sub.3
CH.sub.2--CH.dbd.CH.sub.2 A-51 CF.sub.3 CH.sub.2--CH.dbd.CH.sub.2
A-52 CHF.sub.2 CH.sub.2--CH.dbd.CH.sub.2 A-53 CH.dbd.CHCH.sub.3
CH.sub.2--CH.dbd.CH.sub.2 A-54 C(CH.sub.3).dbd.CH.sub.2
CH.sub.2--CH.dbd.CH.sub.2 A-55 1-(Cl)-cyclopropyl
CH.sub.2--CH.dbd.CH.sub.2 A-56 1-(F)-cyclopropyl
CH.sub.2--CH.dbd.CH.sub.2 A-57 H CH.sub.2--C.ident.C--H A-58
CH.sub.3 CH.sub.2--C.ident.C--H A-59 CH.sub.2CH.sub.3
CH.sub.2--C.ident.C--H A-60 CH(CH.sub.3).sub.2
CH.sub.2--C.ident.C--H A-61 C.sub.3H.sub.5 CH.sub.2--C.ident.C--H
(cyclopropyl) A-62 C.sub.4H.sub.7 (cyclobutyl)
CH.sub.2--C.ident.C--H A-63 C.ident.CCH.sub.3
CH.sub.2--C.ident.C--H A-64 C(CH.sub.3).sub.3
CH.sub.2--C.ident.C--H A-65 CF.sub.3 CH.sub.2--C.ident.C--H A-66
CHF.sub.2 CH.sub.2--C.ident.C--H A-67 CH.dbd.CHCH.sub.3
CH.sub.2--C.ident.C--H A-68 C(CH.sub.3).dbd.CH.sub.2
CH.sub.2--C.ident.C--H A-69 1-(Cl)-cyclopropyl
CH.sub.2--C.ident.C--H A-70 1-(F)-cyclopropyl
CH.sub.2--C.ident.C--H
TABLE-US-00006 TABLE B No. (R.sup.4.sub.m) B-1 --* B-2 2-Cl B-3
3-Cl B-4 2-F B-5 3-F B-6 2-CN B-7 3-CN B-8 4-CN B-9 2-NO.sub.2 B-10
3-NO.sub.2 B-11 4-NO.sub.2 B-12 2-SCH.sub.3 B-13 3-SCH.sub.3 B-14
4-SCH.sub.3 B-15 2-SOCH.sub.3 B-16 3-SOCH.sub.3 B-17 4-SOCH.sub.3
B-18 2-SO.sub.2CH.sub.3 B-19 3-SO.sub.2CH.sub.3 B-20
4-SO.sub.2CH.sub.3 B-21 2-CO.sub.2CH.sub.3 B-22 3-CO.sub.2CH.sub.3
B-23 4-CO.sub.2CH.sub.3 B-24 2,3-Cl.sub.2 B-25 2,4-Cl.sub.2 B-26
2,5-Cl.sub.2 B-27 3,4-Cl.sub.2 B-28 3,5-Cl.sub.2 B-29 2,6-Cl.sub.2
B-30 2,3-F.sub.2 B-31 2,4-F.sub.2 B-32 2,5-F.sub.2 B-33 3,4-F.sub.2
B-34 3,5-F.sub.2 B-35 2,6-F.sub.2 B-36 2-F-3-Cl B-37 2-F-4-Cl B-38
3-F-4-Cl B-39 2-F-6-Cl B-40 2-Cl-3-F B-41 2-Cl-4-F B-42 3-Cl-4-F
B-43 2,3,4-Cl.sub.3 B-44 2,4,5-Cl.sub.3 B-45 3,4,5-Cl.sub.3 B-46
2,4,6-Cl.sub.3 B-47 2,3,4-F.sub.3 B-48 2,4,5-F.sub.3 B-49
3,4,5-F.sub.3 B-50 2,4,6-F.sub.3 B-51 2,3,4-F.sub.3 B-52
2,4-F.sub.2-3-Cl B-53 2,6-F.sub.2-4-Cl B-54 2,5-F.sub.2-4-Cl B-55
2,4-Cl.sub.2-3-F B-56 2,6-Cl.sub.2-4-F B-57 2,5-Cl.sub.2-4-F B-58
2-CH.sub.3 B-59 3-CH.sub.3 B-60 4-CH.sub.3 B-61 2-CH.sub.2CH.sub.3
B-62 3-CH.sub.2CH.sub.3 B-63 4-CH.sub.2CH.sub.3 B-64 2-CF.sub.3
B-65 3-CF.sub.3 B-66 4-CF.sub.3 B-67 2-CHF.sub.2 B-68 3-CHF.sub.2
B-69 4-CHF.sub.2 B-70 2-OCH.sub.3 B-71 3-OCH.sub.3 B-72 4-OCH.sub.3
B-73 2-OCH.sub.2CH.sub.3 B-74 3-OCH.sub.2CH.sub.3 B-75
4-OCH.sub.2CH.sub.3 B-76 2-OCF.sub.3 B-77 3-OCF.sub.3 B-78
4-OCF.sub.3 B-79 2-OCHF.sub.2 B-80 3-OCHF.sub.2 B-81 4-OCHF.sub.2
B-82 2,3-(CH.sub.3).sub.2 B-83 2,4-(CH.sub.3).sub.2 B-84
3,4-(CH.sub.3).sub.2 B-85 2,6-(CH.sub.3).sub.2 B-86
2,3-(CH.sub.2CH.sub.3).sub.2 B-87 2,4-(CH.sub.2CH.sub.3).sub.2 B-88
3,4-(CH.sub.2CH.sub.3).sub.2 B-89 2,6-(CH.sub.2CH.sub.3).sub.2 B-90
2,3-(CF.sub.3).sub.2 B-91 2,4-(CF.sub.3).sub.2 B-92
3,4-(CF.sub.3).sub.2 B-93 2,6-(CF.sub.3).sub.2 B-94
2,3-(CHF.sub.2).sub.2 B-95 2,4-(CHF.sub.2).sub.2 B-96
3,4-(CHF.sub.2).sub.2 B-97 2,6-(CHF.sub.2).sub.2 B-98
2,3-(OCH.sub.3).sub.2 B-99 2,4-(OCH.sub.3).sub.2 B-100
3,4-(OCH.sub.3).sub.2 B-101 2,6-(OCH.sub.3).sub.2 B-102
2,3-(OCH.sub.2CH.sub.3).sub.2 B-103 2,4-(OCH.sub.2CH.sub.3).sub.2
B-104 3,4-(OCH.sub.2CH.sub.3).sub.2 B-105
2,6-(OCH.sub.2CH.sub.3).sub.2 B-106 2,3-(OCF.sub.3).sub.2 B-107
2,4-(OCF.sub.3).sub.2 B-108 3,4-(OCF.sub.3).sub.2 B-109
2,6-(OCF.sub.3).sub.2 B-110 2,3-(OCHF.sub.2).sub.2 B-111
2,4-(OCHF.sub.2).sub.2 B-112 3,4-(OCHF.sub.2).sub.2 B-113
2,6-(OCHF.sub.2).sub.2 B-114 2,3,4-(CH.sub.3).sub.3 B-115
2,4,5-(CH.sub.3).sub.3 B-116 3,4,5-(CH.sub.3).sub.3 B-117
2,4,6-(CH.sub.3).sub.3 B-118 2,3,4-(CH.sub.2CH.sub.3).sub.3 B-119
2,4,5-(CH.sub.2CH.sub.3).sub.3 B-120 3,4,5-(CH.sub.2CH.sub.3).sub.3
B-121 2,4,6-(CH.sub.2CH.sub.3).sub.3 B-122 2,3,4-(CF.sub.3).sub.3
B-123 2,4,5-(CF.sub.3).sub.3 B-124 3,4,5-(CF.sub.3).sub.3 B-125
2,4,6-(CF.sub.3).sub.3 B-126 2,3,4-(CHF.sub.2).sub.3 B-127
2,4,5-(CHF.sub.2).sub.3 B-128 3,4,5-(CHF.sub.2).sub.3 B-129
2,4,6-(CHF.sub.2).sub.3 B-130 2,3,4-(OCH.sub.3).sub.3 B-131
2,4,5-(OCH.sub.3).sub.3 B-132 3,4,5-(OCH.sub.3).sub.3 B-133
2,4,6-(OCH.sub.3).sub.3 B-134 2,3,4-(OCH.sub.2CH.sub.3).sub.3 B-135
2,4,5-(OCH.sub.2CH.sub.3).sub.3 B-136
3,4,5-(OCH.sub.2CH.sub.3).sub.3 B-137
2,4,6-(OCH.sub.2CH.sub.3).sub.3 B-138 2,3,4-(OCF.sub.3).sub.3 B-139
2,4,5-(OCF.sub.3).sub.3 B-140 3,4,5-(OCF.sub.3).sub.3 B-141
2,4,6-(OCF.sub.3).sub.3 B-142 2,3,4-(OCHF.sub.2).sub.3 B-143
2,4,5-(OCHF.sub.2).sub.3 B-144 3,4,5-(OCHF.sub.2).sub.3 B-145
2,4,6-(OCHF.sub.2).sub.3 B-146 2-CF.sub.3-4-Cl B-147 2-CF.sub.3-4-F
B-148 2-Cl-4-CF.sub.3 B-149 2-F-4-CF.sub.3 B-150 2-CN-4-Cl B-151
2-CN-4-F B-152 2-Cl-4-CN B-153 2-F-4-CN
[0397] The compounds I and the compositions according to the
invention, respectively, are suitable as fungicides.
[0398] Consequently, according to a further aspect, the present
invention relates to the use of compounds of formula I, the
N-oxides and the agriculturally acceptable salts thereof or of the
compositions of the invention for combating phytopathogenic
fungi.
[0399] Accordingly, the present invention also encompasses a method
for combating harmful fungi, comprising treating the fungi or the
materials, plants, the soil or seeds to be protected against fungal
attack with an effective amount of at least one compound of formula
I or with a composition comprising according to the invention.
[0400] They are distinguished by an outstanding effectiveness
against a broad spectrum of phytopathogenic fungi, including
soil-borne fungi, which derive especially from the classes of the
Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes),
Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and
Deuteromycetes (syn. Fungi imperfecti). Some are systemically
effective and they can be used in crop protection as foliar
fungicides, fungicides for seed dressing and soil fungicides.
Moreover, they are suitable for controlling harmful fungi, which
inter alia occur in wood or roots of plants.
[0401] The compounds I and the compositions according to the
invention are particularly important in the control of a multitude
of phytopathogenic fungi on various cultivated plants, such as
cereals, e.g. wheat, rye, barley, triticale, oats or rice; beet,
e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits
or soft fruits, e.g. apples, pears, plums, peaches, almonds,
cherries, strawberries, raspberries, blackberries or gooseberries;
leguminous plants, such as lentils, peas, alfalfa or soybeans; oil
plants, such as rape, mustard, olives, sunflowers, coconut, cocoa
beans, castor oil plants, oil palms, ground nuts or soybeans;
cucurbits, such as squashes, cucumber or melons; fiber plants, such
as cotton, flax, hemp or jute; citrus fruit, such as oranges,
lemons, grapefruits or mandarins; vegetables, such as spinach,
lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes,
cucurbits or paprika; lauraceous plants, such as avocados, cinnamon
or camphor; energy and raw material plants, such as corn, soybean,
rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea;
bananas; vines (table grapes and grape juice grape vines); hop;
turf; sweet leaf (also called Stevia); natural rubber plants or
ornamental and forestry plants, such as flowers, shrubs,
broad-leaved trees or evergreens, e.g. conifers; and on the plant
propagation material, such as seeds, and the crop material of these
plants.
[0402] Preferably, compounds I and compositions thereof,
respectively are used for controlling a multitude of fungi on field
crops, such as potatoes sugar beets, tobacco, wheat, rye, barley,
oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers,
coffee or sugar cane; fruits; vines; ornamentals; or vegetables,
such as cucumbers, tomatoes, beans or squashes.
[0403] The term "plant propagation material" is to be understood to
denote all the generative parts of the plant such as seeds and
vegetative plant material such as cuttings and tubers (e.g.
potatoes), which can be used for the multiplication of the plant.
This includes seeds, roots, fruits, tubers, bulbs, rhizomes,
shoots, sprouts and other parts of plants, including seedlings and
young plants, which are to be transplanted after germination or
after emergence from soil. These young plants may also be protected
before transplantation by a total or partial treatment by immersion
or pouring.
[0404] Preferably, treatment of plant propagation materials with
compounds I and compositions thereof, respectively, is used for
controlling a multitude of fungi on cereals, such as wheat, rye,
barley and oats; rice, corn, cotton and soybeans.
[0405] The term "cultivated plants" is to be understood as
including plants which have been modified by breeding, mutagenesis
or genetic engineering including but not limiting to agricultural
biotech products on the market or in development (cf.
http://cera-gmc.org/, see GM crop database therein). Genetically
modified plants are plants, which genetic material has been so
modified by the use of recombinant DNA techniques that under
natural circumstances cannot readily be obtained by cross breeding,
mutations or natural recombination. Typically, one or more genes
have been integrated into the genetic material of a genetically
modified plant in order to improve certain properties of the plant.
Such genetic modifications also include but are not limited to
targeted post-translational modification of protein(s), oligo- or
polypeptides e.g. by glycosylation or polymer additions such as
prenylated, acetylated or farnesylated moieties or PEG
moieties.
[0406] Plants that have been modified by breeding, mutagenesis or
genetic engineering, e.g. have been rendered tolerant to
applications of specific classes of herbicides, such as auxin
herbicides such as dicamba or 2,4-D; bleacher herbicides such as
hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene
desaturase (PDS) inhibittors; acetolactate synthase (ALS)
inhibitors such as sulfonyl ureas or imidazolinones;
enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such
as glyphosate; glutamine synthetase (GS) inhibitors such as
glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid
biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase)
inhibitors; or oxynil (i.e. bromoxynil or ioxynil) herbicides as a
result of conventional methods of breeding or genetic engineering.
Furthermore, plants have been made resistant to multiple classes of
herbicides through multiple genetic modifications, such as
resistance to both glyphosate and glufosinate or to both glyphosate
and a herbicide from another class such as ALS inhibitors, HPPD
inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide
resistance technologies are e.g. described in Pest Managem. Sci.
61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61,
2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108;
Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185;
and references quoted therein. Several cultivated plants have been
rendered tolerant to herbicides by conventional methods of breeding
(mutagenesis), e.g. Clearfield.RTM. summer rape (Canola, BASF SE,
Germany) being tolerant to imidazolinones, e.g. imazamox, or
ExpressSun.RTM. sunflowers (DuPont, USA) being tolerant to sulfonyl
ureas, e.g. tribenuron. Genetic engineering methods have been used
to render cultivated plants such as soybean, cotton, corn, beets
and rape, tolerant to herbicides such as glyphosate and
glufosinate, some of which are commercially available under the
trade names RoundupReady.RTM. (glyphosate-tolerant, Monsanto,
U.S.A.), Cultivance.RTM. (imidazolinone tolerant, BASF SE, Germany)
and LibertyLink.RTM. (glufosinate-tolerant, Bayer CropScience,
Germany).
[0407] Furthermore, plants are also covered that are by the use of
recombinant DNA techniques capable to synthesize one or more
insecticidal proteins, especially those known from the bacterial
genus Bacillus, particularly from Bacillus thuringiensis, such as
5-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b),
CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins
(VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of
bacteria colonizing nematodes, e.g. Photorhabdus spp. or
Xenorhabdus spp.; toxins produced by animals, such as scorpion
toxins, arachnid toxins, wasp toxins, or other insect-specific
neurotoxins; toxins produced by fungi, such Streptomycetes toxins,
plant lectins, such as pea or barley lectins; agglutinins;
proteinase inhibitors, such as trypsin inhibitors, serine protease
inhibitors, patatin, cystatin or papain inhibitors;
ribosome-inactivating proteins (RIP), such as ricin, maize-RIP,
abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such
as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,
cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion
channel blockers, such as blockers of sodium or calcium channels;
juvenile hormone esterase; diuretic hormone receptors (helicokinin
receptors); stilben synthase, bibenzyl synthase, chitinases or
glucanases. In the context of the present invention these
insecticidal proteins or toxins are to be understood expressly also
as pre-toxins, hybrid proteins, truncated or otherwise modified
proteins. Hybrid proteins are characterized by a new combination of
protein domains, (see, e.g. WO 02/015701). Further examples of such
toxins or genetically modified plants capable of synthesizing such
toxins are disclosed, e.g., in EP-A 374 753, WO 93/007278, WO
95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073.
The methods for producing such genetically modified plants are
generally known to the person skilled in the art and are described,
e.g. in the publications mentioned above. These insecticidal
proteins contained in the genetically modified plants impart to the
plants producing these proteins tolerance to harmful pests from all
taxonomic groups of athropods, especially to beetles (Coeloptera),
two-winged insects (Diptera), and moths (Lepidoptera) and to
nematodes (Nematoda). Genetically modified plants capable to
synthesize one or more insecticidal proteins are, e.g., described
in the publications mentioned above, and some of which are
commercially available such as YieldGard.RTM. (corn cultivars
producing the CryIAb toxin), YieldGard.RTM. Plus (corn cultivars
producing CryIAb and Cry3Bb1 toxins), Starlink.RTM. (corn cultivars
producing the Cry9c toxin), Herculex.RTM. RW (corn cultivars
producing Cry34Ab1, Cry35Ab1 and the enzyme
Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN.RTM. 33B
(cotton cultivars producing the CryIAc toxin), Bollgard.RTM. I
(cotton cultivars producing the CryIAc toxin), Bollgard.RTM. II
(cotton cultivars producing CryIAc and Cry2Ab2 toxins); VIPCOT.RTM.
(cotton cultivars producing a VIP-toxin); NewLeaf.RTM. (potato
cultivars producing the Cry3A toxin); Bt-Xtra.RTM.,
NatureGard.RTM., KnockOut.RTM., BiteGard.RTM., Protecta.RTM., Bt11
(e.g. Agrisure.RTM. CB) and Bt176 from Syngenta Seeds SAS, France,
(corn cultivars producing the CryIAb toxin and PAT enyzme), MIR604
from Syngenta Seeds SAS, France (corn cultivars producing a
modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863
from Monsanto Europe S.A., Belgium (corn cultivars producing the
Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton
cultivars producing a modified version of the CryIAc toxin) and
1507 from Pioneer Overseas Corporation, Belgium (corn cultivars
producing the CryIF toxin and PAT enzyme).
[0408] Furthermore, plants are also covered that are by the use of
recombinant DNA techniques capable to synthesize one or more
proteins to increase the resistance or tolerance of those plants to
bacterial, viral or fungal pathogens. Examples of such proteins are
the so-called "pathogenesisrelated proteins" (PR proteins, see,
e.g. EP-A 392 225), plant disease resistance genes (e.g. potato
cultivars, which express resistance genes acting against
Phytophthora infestans derived from the mexican wild potato Solanum
bulbocastanum) or T4-lysozym (e.g. potato cultivars capable of
synthesizing these proteins with increased resistance against
bacteria such as Erwinia amylvora). The methods for producing such
genetically modified plants are generally known to the person
skilled in the art and are described, e.g. in the publications
mentioned above.
[0409] Furthermore, plants are also covered that are by the use of
recombinant DNA techniques capable to synthesize one or more
proteins to increase the productivity (e.g. bio mass production,
grain yield, starch content, oil content or protein content),
tolerance to drought, salinity or other growth-limiting
environmental factors or tolerance to pests and fungal, bacterial
or viral pathogens of those plants.
[0410] Furthermore, plants are also covered that contain by the use
of recombinant DNA techniques a modified amount of substances of
content or new substances of content, specifically to improve human
or animal nutrition, e.g. oil crops that produce health-promoting
long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids
(e.g. Nexera.RTM. rape, DOW Agro Sciences, Canada).
[0411] Furthermore, plants are also covered that contain by the use
of recombinant DNA techniques a modified amount of substances of
content or new substances of content, specifically to improve raw
material production, e.g. potatoes that produce increased amounts
of amylopectin (e.g. Amflora.RTM. potato, BASF SE, Germany).
[0412] The compounds I and compositions thereof, respectively, are
particularly suitable for controlling the following plant
diseases:
[0413] Albugo spp. (white rust) on ornamentals, vegetables (e.g. A.
candida) and sunflowers (e.g. A. tragopogonis); Alternaria spp.
(Alternaria leaf spot) on vegetables, rape (A. brassicola or
brassicae), sugar beets (A. tenuis), fruits, rice, soybeans,
potatoes (e.g. A. solani or A. alternata), tomatoes (e.g. A. solani
or A. alternata) and wheat; Aphanomyces spp. on sugar beets and
vegetables; Ascochyta spp. on cereals and vegetables, e.g. A.
tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris
and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. Southern
leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on
corn, e.g. spot blotch (B. sorodniana) on cereals and e.g. B.
oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis
(powdery mildew) on cereals (e.g. on wheat or barley); Botrytis
cinerea (teleomorph: Bottyotinia fuckeliana: grey mold) on fruits
and berries (e.g. strawberries), vegetables (e.g. lettuce, carrots,
celery and cabbages), rape, flowers, vines, forestry plants and
wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis
(syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and
evergreens, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora
spp. (Cercospora leaf spots) on corn (e.g. Gray leaf spot: C.
zeae-maydis), rice, sugar beets (e.g. C. beticola), sugar cane,
vegetables, coffee, soybeans (e.g. C. solina or C. kikuchii) and
rice; Cladosporium spp. on tomatoes (e.g. C. fulvum: leaf mold) and
cereals, e.g. C. herbarum (black ear) on wheat; ClaviCeps purpurea
(ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of
Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e.g.
C. sativus, anamorph: B. sorokiniana) and rice (e.g. C. miyabeanus,
anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp.
(anthracnose) on cotton (e.g. C. gossypii), corn (e.g. C.
graminicola: Anthracnose stalk rot), soft fruits, potatoes (e.g. C.
coccodes: black dot), beans (e.g. C. lindemuthianum) and soybeans
(e.g. C. truncatum or C. gloeosporiodes); Corticium spp., e.g. C.
sasakii (sheath blight) on rice; Corynespora cassiicola (leaf
spots) on soybeans and ornamentals; Cycloconium spp., e.g. C.
oleaginum on olive trees; Cylindrocarpon spp. (e.g. fruit tree
canker or young vine decline, teleomorph: Nectria or Neonectna
spp.) on fruit trees, vines (e.g. C. liriodendri, teleomorph:
Neonectria liriodendri: Black Foot Disease) and ornamentals;
Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot)
on soybeans; Diaporthe spp., e.g. D. phaseolorum (damping off) on
soybeans; Drechslera (syn. Helminthosporium, teleomorph:
Pyrenophora) spp. on corn, cereals, such as barley (e.g. D. teres,
net blotch) and wheat (e.g. D. tritici-repentis: tan spot), rice
and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia
(syn. Phellinus) punctata, F. mediterranea, Phaeomoniella
chlamydospora (earlier Phaeoacremonium chlamydosporum),
Phaeoacremonium aleophlium and/or Botryosphaeria obtusa; Elsinoe
spp. on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose)
and vines (E. ampelina: anthracnose); Entyloma oryzae (leaf smut)
on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp.
(powdery mildew) on sugar beets (E. betae), vegetables (e.g. E.
pisi), such as cucurbits (e.g. E. cichoracearum), cabbages, rape
(e.g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback,
anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit
trees, vines and ornamental woods; Exserohllum (syn.
Helminthosporium) spp. on corn (e.g. E. turcicum); Fusarium
(teleomorph: Gibberella) spp. (wilt, root or stem rot) on various
plants, such as F. graminearum or F. culmorum (root rot, scab or
head blight) on cereals (e.g. wheat or barley), F. oxysporum on
tomatoes, F. solani f. sp. glycines now syn. F. virguliforme) and
F. tucumaniae and F. brasiliense each causing sudden death syndrome
on soybeans and F. verticilliodes on corn; Gaeumannomyces graminis
(take-all) on cereals (e.g. wheat or barley) and corn; Gibberella
spp. on cereals (e.g. G. zeae) and rice (e.g. G. fujikuroi: Bakanae
disease); Glomerella angulata on vines, pome fruits and other
plants and G. gossypii on cotton; Grainstaining complex on rice;
Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on
rosaceous plants and junipers, e.g. G. sabinae (rust) on pears;
Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus)
on corn, cereals and rice; Hemileia spp., e.g. H. vastatrix (coffee
leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium
vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and
stem rot) on soybeans and cotton; Microdochium (syn. Fusarium)
nivale (pink snow mold) on cereals (e.g. wheat or barley);
Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp.,
e.g. M. laxa, M. fructicola and M. fructigena (bloom and twig
blight, brown rot) on stone fruits and other rosaceous plants;
Mycosphaerella spp. on cereals, bananas, soft fruits and ground
nuts, such as e.g. M. graminicola (anamorph: Septoria tritici,
Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease)
on bananas; Peronospora spp. (downy mildew) on cabbage (e.g. P.
brassicae), rape (e.g. P. parasitica), onions (e.g. P. destructor),
tobacco (P. tabacina) and soybeans (e.g. P. manshurica); Phakopsora
pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora
spp. e.g. on vines (e.g. P. tracheiphila and P. tetraspora) and
soybeans (e.g. P. gregata: stem rot); Phoma lingam (root and stem
rot) on rape and cabbage and P. betae (root rot, leaf spot and
damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines
(e.g. P. viticola: can and leaf spot) and soybeans (e.g. stem rot:
P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydiS
(brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit
and stem root) on various plants, such as paprika and cucurbits
(e.g. P. capsici), soybeans (e.g. P. megasperma, syn. P. sojae),
potatoes and tomatoes (e.g. P. infestans late blight) and
broad-leaved trees (e.g. P. ramorum: sudden oak death);
Plasmodiophora brassicae (club root) on cabbage, rape, radish and
other plants; Plasmopara spp., e.g. P. viticola (grapevine downy
mildew) on vines and P. halstedii on sunflowers; Podosphaera spp.
(powdery mildew) on rosaceous plants, hop, pome and soft fruits,
e.g. P. leucotricha on apples; Polymyxa spp., e.g. on cereals, such
as barley and wheat (P. graminis) and sugar beets (P. betae) and
thereby transmitted viral diseases; Pseudocercosporella
herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on
cereals, e.g. wheat or barley; Pseudoperonospora (downy mildew) on
various plants, e.g. P. cubensis on cucurbits or P. humili on hop;
Pseudopezicula tracheiphila (red fire disease or `rotbrenner`,
anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various
plants, e.g. P. triticina (brown or leaf rust), P. striiformis
(stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem
or black rust) or P. recondita (brown or leaf rust) on cereals,
such as e.g. wheat, barley or rye, P. kuehnii (orange rust) on
sugar cane and P. asparagion asparagus; Pyrenophora (anamorph:
Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net
blotch) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph:
Magnaporthe grisea, rice blast) on rice and P. grisea on turf and
cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat,
cotton, rape, sunflowers, soybeans, sugar beets, vegetables and
various other plants (e.g. P. ultimum or P. aphanidermatum);
Ramularia spp., e.g. R. collo-cygni (Ramularia leaf spots,
Physiological leaf spots) on barley and R. beticola on sugar beets;
Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape,
potatoes, sugar beets, vegetables and various other plants, e.g. R.
solani (root and stem rot) on soybeans, R. solani (sheath blight)
on rice or R. cerealis (Rhizoctonia spring blight) on wheat or
barley; Rhizopus stolonifer (black mold, soft rot) on strawberries,
carrots, cabbage, vines and tomatoes; Rhynchosporium secalis
(scald) on barley, rye and triticale; Sarocladium oryzae and S.
attenuatum (sheath rot) on rice; Sclerotima spp. (stem rot or white
mold) on vegetables and field crops, such as rape, sunflowers (e.g.
S. sclerotiorum) and soybeans (e.g. S. rolfsii or S. sclerotiorum);
Septoria spp. on various plants, e.g. S. glycines (brown spot) on
soybeans, S. tritici(Septoria blotch) on wheat and S. (syn.
Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula
(syn. Erysiphe) necator (powdery mildew, anamorph: Odium tuckeri)
on vines; Setospaeria spp. (leaf blight) on corn (e.g. S. turcicum,
syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut)
on corn, (e.g. S. reiliana: head smut), sorghum and sugar cane;
Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora
subterranea (powdery scab) on potatoes and thereby transmitted
viral diseases; Stagonospora spp. on cereals, e.g. S. nodorum
(Stagonospora blotch, teleomorph: Leptosphaeria [syn.
Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on
potatoes (potato wart disease); Taphrina spp., e.g. T. deformans
(leaf curl disease) on peaches and T. pruni (plum pocket) on plums;
Thielaviopsis spp. (black root rot) on tobacco, pome fruits,
vegetables, soybeans and cotton, e.g. T. basicola (syn. Chalara
elegans); Tilletia spp. (common bunt or stinking smut) on cereals,
such as e.g. T. tritici (syn. T caries, wheat bunt) and T.
controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow
mold) on barley or wheat; Urocystis spp., e.g. U. occulta (stem
smut) on rye; Uromyces spp. (rust) on vegetables, such as beans
(e.g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e.g. U.
betae); Ustilago spp. (loose smut) on cereals (e.g. U. nuda and U.
avaenae), corn (e.g. U. maydis: corn smut) and sugar cane; Venturia
spp. (scab) on apples (e.g. V. inaequalis) and pears; and
Verticillium spp. (wilt) on various plants, such as fruits and
ornamentals, vines, soft fruits, vegetables and field crops, e.g.
V. dahliae on strawberries, rape, potatoes and tomatoes.
[0414] The compounds I and compositions thereof, respectively, are
also suitable for controlling harmful fungi in the protection of
stored products or harvest and in the protection of materials. The
term "protection of materials" is to be understood to denote the
protection of technical and nonliving materials, such as adhesives,
glues, wood, paper and paperboard, textiles, leather, paint
dispersions, plastics, coiling lubricants, fiber or fabrics,
against the infestation and destruction by harmful microorganisms,
such as fungi and bacteria. As to the protection of wood and other
materials, the particular attention is paid to the following
harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis
spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp.,
Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such
as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus
spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp.,
Deuteromycetes such as Aspergillus spp., Cladosporium spp.,
Penicillium spp., Trichorma spp., Alternaria spp., Paecilomyces
spp. and Zygomycetes such as Mucor spp., and in addition in the
protection of stored products and harvest the following yeast fungi
are worthy of note: Candida spp. and Saccharomyces cerevisae.
[0415] The method of treatment according to the invention can also
be used in the field of protecting stored products or harvest
against attack of fungi and microorganisms. According to the
present invention, the term "stored products" is understood to
denote natural substances of plant or animal origin and their
processed forms, which have been taken from the natural life cycle
and for which long-term protection is desired. Stored products of
crop plant origin, such as plants or parts thereof, for example
stalks, leafs, tubers, seeds, fruits or grains, can be protected in
the freshly harvested state or in processed form, such as
pre-dried, moistened, comminuted, ground, pressed or roasted, which
process is also known as post-harvest treatment. Also falling under
the definition of stored products is timber, whether in the form of
crude timber, such as construction timber, electricity pylons and
barriers, or in the form of finished articles, such as furniture or
objects made from wood. Stored products of animal origin are hides,
leather, furs, hairs and the like. The combinations according the
present invention can prevent disadvantageous effects such as
decay, discoloration or mold. Preferably "stored products" is
understood to denote natural substances of plant origin and their
processed forms, more preferably fruits and their processed forms,
such as pomes, stone fruits, soft fruits and citrus fruits and
their processed forms.
[0416] The compounds I and compositions thereof, respectively, may
be used for improving the health of a plant. The invention also
relates to a method for improving plant health by treating a plant,
its propagation material and/or the locus where the plant is
growing or is to grow with an effective amount of compounds I and
compositions thereof, respectively.
[0417] The term "plant health" is to be understood to denote a
condition of the plant and/or its products which is determined by
several indicators alone or in combination with each other such as
yield (e.g. increased biomass and/or increased content of valuable
ingredients), plant vigor (e.g. improved plant growth and/or
greener leaves ("greening effect")), quality (e.g. improved content
or composition of certain ingredients) and tolerance to abiotic
and/or biotic stress. The above identified indicators for the
health condition of a plant may be interdependent or may result
from each other.
[0418] The compounds of formula I can be present in different
crystal modifications whose biological activity may differ. They
are likewise subject matter of the present invention.
[0419] The compounds I are employed as such or in form of
compositions by treating the fungi or the plants, plant propagation
materials, such as seeds, soil, surfaces, materials or rooms to be
protected from fungal attack with a fungicidally effective amount
of the active substances. The application can be carried out both
before and after the infection of the plants, plant propagation
materials, such as seeds, soil, surfaces, materials or rooms by the
fungi.
[0420] Plant propagation materials may be treated with compounds I
as such or a composition comprising at least one compound I
prophylactically either at or before planting or transplanting.
[0421] The invention also relates to compositions comprising one
compound I according to the invention. In particular, such
composition further comprises an auxiliary as defined below.
[0422] The term "effective amount" used denotes an amount of the
composition or of the compounds I, which is sufficient for
controlling harmful fungi on cultivated plants or in the protection
of materials and which does not result in a substantial damage to
the treated plants. Such an amount can vary in a broad range and is
dependent on various factors, such as the fungal species to be
controlled, the treated cultivated plant or material, the climatic
conditions and the specific compound I used.
[0423] The compounds I, their N-oxides and salts can be converted
into customary types of agrochemical compositions, e.g. solutions,
emulsions, suspensions, dusts, powders, pastes, granules,
pressings, capsules, and mixtures thereof. Examples for composition
types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates
(e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC),
pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP,
DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG,
GG, MG), insecticidal articles (e.g. LN), as well as gel
formulations for the treatment of plant propagation materials such
as seeds (e.g. GF). These and further compositions types are
defined in the "Catalogue of pesticide formulation types and
international coding system", Technical Monograph No. 2, 6.sup.th
Ed. May 2008, CropLife International.
[0424] The compositions are prepared in a known manner, such as
described by Mollet and Grubemann, Formulation technology, Wiley
VCH, Weinheim, 2001; or Knowles, New developments in crop
protection product formulation, Agrow Reports DS243, T&F
Informa, London, 2005.
[0425] Suitable auxiliaries are solvents, liquid carriers, solid
carriers or fillers, surfactants, dispersants, emulsifiers,
wetters, adjuvants, solubilizers, penetration enhancers, protective
colloids, adhesion agents, thickeners, humectants, repellents,
attractants, feeding stimulants, compatibilizers, bactericides,
anti-freezing agents, anti-foaming agents, colorants, tackifiers
and binders.
[0426] Suitable solvents and liquid carriers are water and organic
solvents, such as mineral oil fractions of medium to high boiling
point, e.g. kerosene, diesel oil; oils of vegetable or animal
origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene,
paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols,
e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol;
glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates,
carbonates, fatty acid esters, gamma-butyrolactone; fatty acids;
phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid
dimethylamides; and mixtures thereof.
[0427] Suitable solid carriers or fillers are mineral earths, e.g.
silicates, silica gels, talc, kaolins, limestone, lime, chalk,
clays, dolomite, diatomaceous earth, bentonite, calcium sulfate,
magnesium sulfate, magnesium oxide; polysaccharides, e.g.
cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium
phosphate, ammonium nitrate, ureas; products of vegetable origin,
e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and
mixtures thereof.
[0428] Suitable surfactants are surface-active compounds, such as
anionic, cationic, nonionic and amphoteric surfactants, block
polymers, polyelectrolytes, and mixtures thereof. Such surfactants
can be used as emulsifier, dispersant, solubilizer, wetter,
penetration enhancer, protective colloid, or adjuvant. Examples of
surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers &
Detergents, McCutcheon's Directories, Glen Rock, USA, 2008
(International Ed. or North American Ed.).
[0429] Suitable anionic surfactants are alkali, alkaline earth or
ammonium salts of sulfonates, sulfates, phosphates, carboxylates,
and mixtures thereof. Examples of sulfonates are
alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates,
lignine sulfonates, sulfonates of fatty acids and oils, sulfonates
of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols,
sulfonates of condensed naphthalenes, sulfonates of dodecyl- and
tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes,
sulfosuccinates or sulfosuccinamates. Examples of sulfates are
sulfates of fatty acids and oils, of ethoxylated alkylphenols, of
alcohols, of ethoxylated alcohols, or of fatty acid esters.
Examples of phosphates are phosphate esters. Examples of
carboxylates are alkyl carboxylates, and carboxylated alcohol or
alkylphenol ethoxylates.
[0430] Suitable nonionic surfactants are alkoxylates, N-subsituted
fatty acid amides, amine oxides, esters, sugar-based surfactants,
polymeric surfactants, and mixtures thereof. Examples of
alkoxylates are compounds such as alcohols, alkylphenols, amines,
amides, arylphenols, fatty acids or fatty acid esters which have
been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or
propylene oxide may be employed for the alkoxylation, preferably
ethylene oxide. Examples of N-subsititued fatty acid amides are
fatty acid glucamides or fatty acid alkanolamides. Examples of
esters are fatty acid esters, glycerol esters or monoglycerides.
Examples of sugar-based surfactants are sorbitans, ethoxylated
sorbitans, sucrose and glucose esters or alkylpolyglucosides.
Examples of polymeric surfactants are home- or copolymers of
vinylpyrrolidone, vinylalcohols, or vinylacetate.
[0431] Suitable cationic surfactants are quaternary surfactants,
for example quaternary ammonium compounds with one or two
hydrophobic groups, or salts of long-chain primary amines. Suitable
amphoteric surfactants are alkylbetains and imidazolines. Suitable
block polymers are block polymers of the A-B or A-B-A type
comprising blocks of polyethylene oxide and polypropylene oxide, or
of the A-B--C type comprising alkanol, polyethylene oxide and
polypropylene oxide. Suitable polyelectrolytes are polyacids or
polybases. Examples of polyacids are alkali salts of polyacrylic
acid or polyacid comb polymers. Examples of polybases are
polyvinylamines or polyethyleneamines.
[0432] Suitable adjuvants are compounds, which have a neglectable
or even no pesticidal activity themselves, and which improve the
biological performance of the compound I on the target. Examples
are surfactants, mineral or vegetable oils, and other auxilaries.
Further examples are listed by Knowles, Adjuvants and additives,
Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
[0433] Suitable thickeners are polysaccharides (e.g. xanthan gum,
carboxymethylcellulose), anorganic clays (organically modified or
unmodified), polycarboxylates, and silicates.
[0434] Suitable bactericides are bronopol and isothiazolinone
derivatives such as alkylisothiazolinones and
benzisothiazolinones.
[0435] Suitable anti-freezing agents are ethylene glycol, propylene
glycol, urea and glycerin.
[0436] Suitable anti-foaming agents are silicones, long chain
alcohols, and salts of fatty acids.
[0437] Suitable colorants (e.g. in red, blue, or green) are
pigments of low water solubility and water-soluble dyes. Examples
are inorganic colorants (e.g. iron oxide, titan oxide, iron
hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and
phthalocyanine colorants).
[0438] Suitable tackifiers or binders are polyvinylpyrrolidons,
polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or
synthetic waxes, and cellulose ethers.
[0439] Examples for composition types and their preparation
are:
i) Water-Soluble Concentrates (SL, LS)
[0440] 10-60 wt % of a compound I and 5-15 wt % wetting agent (e.g.
alcohol alkoxylates) are dissolved in water and/or in a
water-soluble solvent (e.g. alcohols) ad 100 wt %. The active
substance dissolves upon dilution with water.
ii) Dispersible Concentrates (DC)
[0441] 5-25 wt % of a compound I and 1-10 wt % dispersant (e.g.
polyvinylpyrrolidone) are dissolved in organic solvent (e.g.
cyclohexanone) ad 100 wt %. Dilution with water gives a
dispersion.
iii) Emulsifiable Concentrates (EC)
[0442] 15-70 wt % of a compound I and 5-10 wt % emulsifiers (e.g.
calcium dodecylbenzenesulfonate and castor oil ethoxylate) are
dissolved in water-insoluble organic solvent (e.g. aromatic
hydrocarbon) ad 100 wt %. Dilution with water gives an
emulsion.
iv) Emulsions (EW, EO, ES)
[0443] 5-40 wt % of a compound I and 1-10 wt % emulsifiers (e.g.
calcium dodecylbenzenesulfonate and castor oil ethoxylate) are
dissolved in 20-40 wt % water-insoluble organic solvent (e.g.
aromatic hydrocarbon). This mixture is introduced into water ad 100
wt % by means of an emulsifying machine and made into a homogeneous
emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
[0444] In an agitated ball mill, 20-60 wt % of a compound I are
comminuted with addition of 2-10 wt % dispersants and wetting
agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2
wt % thickener (e.g. xanthan gum) and water ad 100 wt % to give a
fine active substance suspension. Dilution with water gives a
stable suspension of the active substance. For FS type composition
up to 40 wt % binder (e.g. polyvinylalcohol) is added.
vi) Water-Dispersible Granules and Water-Soluble Granules (WG,
SG)
[0445] 50-80 wt % of a compound I are ground finely with addition
of dispersants and wetting agents (e.g. sodium lignosulfonate and
alcohol ethoxylate) ad 100 wt % and prepared as water-dispersible
or water-soluble granules by means of technical appliances (e.g.
extrusion, spray tower, fluidized bed). Dilution with water gives a
stable dispersion or solution of the active substance.
vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP,
WS)
[0446] 50-80 wt % of a compound I are ground in a rotor-stator mill
with addition of 1-5 wt % dispersants (e.g. sodium lignosulfonate),
1-3 wt % wetting agents (e.g. alcohol ethoxylate) and solid carrier
(e.g. silica gel) ad 100 wt %. Dilution with water gives a stable
dispersion or solution of the active substance.
viii) Gel (GW, GF)
[0447] In an agitated ball mill, 5-25 wt % of a compound I are
comminuted with addition of 3-10 wt % dispersants (e.g. sodium
lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose)
and water ad 100 wt % to give a fine suspension of the active
substance. Dilution with water gives a stable suspension of the
active substance.
ix) Microemulsion (ME)
[0448] 5-20 wt % of a compound I are added to 5-30 wt % organic
solvent blend (e.g. fatty acid dimethylamide and cyclohexanone),
10-25 wt % surfactant blend (e.g. alcohol ethoxylate and arylphenol
ethoxylate), and water ad 100%. This mixture is stirred for 1 h to
produce spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS)
[0449] An oil phase comprising 5-50 wt % of a compound I, 0-40 wt %
water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15
wt % acrylic monomers (e.g. methylmethacrylate, methacrylic acid
and a di- or triacrylate) are dispersed into an aqueous solution of
a protective colloid (e.g. polyvinyl alcohol). Radical
polymerization initiated by a radical initiator results in the
formation of poly(meth)acrylate microcapsules. Alternatively, an
oil phase comprising 5-50 wt % of a compound I according to the
invention, 0-40 wt % water insoluble organic solvent (e.g. aromatic
hydrocarbon), and an isocyanate monomer (e.g.
diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous
solution of a protective colloid (e.g. polyvinyl alcohol). The
addition of a polyamine (e.g. hexamethylenediamine) results in the
formation of polyurea microcapsules. The monomers amount to 1-10 wt
%. The wt % relate to the total CS composition.
xi) Dustable powders (DP, DS)
[0450] 1-10 wt % of a compound I are ground finely and mixed
intimately with solid carrier (e.g. finely divided kaolin) ad 100
wt %.
xii) Granules (GR, FG)
[0451] 0.5-30 wt % of a compound I is ground finely and associated
with solid carrier (e.g. silicate) ad 100 wt %. Granulation is
achieved by extrusion, spray-drying or fluidized bed.
xiii) Ultra-low volume liquids (UL)
[0452] 1-50 wt % of a compound I are dissolved in organic solvent
(e.g. aromatic hydrocarbon) ad 100 wt %.
[0453] The compositions types i) to xiii) may optionally comprise
further auxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt %
anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt
% colorants.
[0454] The agrochemical compositions generally comprise between
0.01 and 95%, preferably between 0.1 and 90%, and in particular
between 0.5 and 75%, by weight of active substance. The active
substances are employed in a purity of from 90% to 100%, preferably
from 95% to 100% (according to NMR spectrum).
[0455] Solutions for seed treatment (LS), Suspoemulsions (SE),
flowable concentrates (FS), powders for dry treatment (DS),
water-dispersible powders for slurry treatment (WS), water-soluble
powders (SS), emulsions (ES), emulsifiable concentrates (EC) and
gels (GF) are usually employed for the purposes of treatment of
plant propagation materials, particularly seeds. The compositions
in question give, after two-to-tenfold dilution, active substance
concentrations of from 0.01 to 60% by weight, preferably from 0.1
to 40%, in the ready-to-use preparations. Application can be
carried out before or during sowing. Methods for applying compound
I and compositions thereof, respectively, on to plant propagation
material, especially seeds include dressing, coating, pelleting,
dusting, soaking and in-furrow application methods of the
propagation material. Preferably, compound I or the compositions
thereof, respectively, are applied on to the plant propagation
material by a method such that germination is not induced, e.g. by
seed dressing, pelleting, coating and dusting.
[0456] When employed in plant protection, the amounts of active
substances applied are, depending on the kind of effect desired,
from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha,
more preferably from 0.05 to 0.9 kg per ha, and in particular from
0.1 to 0.75 kg per ha.
[0457] In treatment of plant propagation materials such as seeds,
e.g. by dusting, coating or drenching seed, amounts of active
substance of from 0.1 g to 10 kg, in particular 0.1 to 1000 g, more
particularly from 1 to 1000 g, specificaly from 1 to 100 g and most
specificaly from 5 to 100 g, per 100 kilogram of plant propagation
material (preferably seeds) are generally required.
[0458] When used in the protection of materials or stored products,
the amount of active substance applied depends on the kind of
application area and on the desired effect. Amounts customarily
applied in the protection of materials are 0.001 g to 2 kg,
preferably 0.005 g to 1 kg, of active substance per cubic meter of
treated material.
[0459] Various types of oils, wetters, adjuvants, fertilizer, or
micronutrients, and further pesticides (e.g. herbicides,
insecticides, fungicides, growth regulators, safeners,
biopesticides) may be added to the active substances or the
compositions comprising them as premix or, if appropriate not until
immediately prior to use (tank mix). These agents can be admixed
with the compositions according to the invention in a weight ratio
of 1:100 to 100:1, preferably 1:10 to 10:1.
[0460] A pesticide is generally a chemical or biological agent
(such as a virus, bacterium, antimicrobial or disinfectant) that
through its effect deters, incapacitates, kills or otherwise
discourages pests. Target pests can include insects, plant
pathogens, weeds, mollusks, birds, mammals, fish, nematodes
(roundworms), and microbes that destroy property, cause nuisance,
spread disease or are vectors for disease. The term pesticides
includes also plant growth regulators that alter the expected
growth, flowering, or reproduction rate of plants; defoliants that
cause leaves or other foliage to drop from a plant, usually to
facilitate harvest; desiccants that promote drying of living
tissues, such as unwanted plant tops; plant activators that
activate plant physiology for defense of against certain pests;
safeners that reduce unwanted herbicidal action of pesticides on
crop plants; and plant growth promoters that affect plant
physiology to increase plant growth, biomass, yield or any other
quality parameter of the harvestable goods of acrop plant.
[0461] Biopesticides are typically created by growing and
concentrating naturally occurring organisms and/or their
metabolites including bacteria and other microbes, fungi, viruses,
nematodes, proteins, etc. They are often considered to be important
components of integrated pest management (IPM) programmes.
[0462] Biopesticides fall into two major classes, microbial and
biochemical pesticides:
[0463] (1) Microbial pesticides consist of bacteria, fungi or
viruses (and often include the metabolites that bacteria and fungi
produce). Entomopathogenic nematodes are also classed as microbial
pesticides, even though they are multi-cellular.
[0464] Biochemical pesticides are naturally occurring substances
that control pests or provide other crop protection uses as defined
below, but are relatively non-toxic to mammals.
[0465] The user applies the composition according to the invention
usually from a predosage device, a knapsack sprayer, a spray tank,
a spray plane, or an irrigation system. Usually, the agrochemical
composition is made up with water, buffer, and/or further
auxiliaries to the desired application concentration and the
ready-to-use spray liquor or the agrochemical composition according
to the invention is thus obtained. Usually, 20 to 2000 liters,
preferably 50 to 400 liters, of the ready-to-use spray liquor are
applied per hectare of agricultural useful area.
[0466] According to one embodiment, individual components of the
composition according to the invention such as parts of a kit or
parts of a composition comprising two or three active ingredients,
may be mixed by the user himself in a spray tank or any other kind
of vessel used for applications (e.g. seed treater drums, seed
pelleting machinery, knapsack sprayer) and further auxiliaries may
be added, if appropriate.
[0467] When living microorganisms, such as pesticides from groups
L1), L3) and L5), form part of such kit, it must be taken care that
choice and amounts of the components (e.g. chemcial pesticidal
agents) and of the further auxiliaries should not influence the
viability of the microbial pesticides in the composition mixed by
the user. Especially for bactericides and solvents, compatibility
with the respective microbial pesticide has to be taken into
account.
[0468] Consequently, one embodiment of the invention is a kit for
preparing a usable pesticidal composition, the kit comprising a) a
composition comprising component 1) as defined herein and at least
one auxiliary; and b) a composition comprising component 2) as
defined herein and at least one auxiliary; and optionally c) a
composition comprising at least one auxiliary and optionally a
further active component 3) as defined herein.
[0469] Mixing the compounds I or the compositions comprising them
in the use form as fungicides with other fungicides results in many
cases in an expansion of the fungicidal spectrum of activity being
obtained or in a prevention of fungicide resistance development.
Furthermore, in many cases, synergistic effects are obtained.
[0470] The following list of pesticides (e.g. pesticidally active
substances and biopesticides), in conjunction with which the
compounds I can be used, is intended to illustrate the possible
combinations but does not limit them:
A) Respiration Inhibitors
[0471] Inhibitors of complex III at Q.sub.o site (e.g.
strobilurins): azoxystrobin, coumethoxystrobin, coumoxystrobin,
dimoxystrobin, enestroburin, fenaminstrobin,
fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl,
metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,
pyrametostrobin, pyraoxystrobin, trifloxystrobin and
2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-
-methoxyiminoN-methyl-acetamide, pyribencarb,
triclopyricarb/chlorodincarb, famoxadone, fenamidone; [0472]
inhibitors of complex III at Q.sub.i site: cyazofamid, amisulbrom,
[(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino-
]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,
[(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbo-
nyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,
[(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-c-
arbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,
[(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyr-
idine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropa-
noate;
(3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]--
6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl2-methylpropanoate,
(3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-meth-
yl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl 2-methylpropanoate;
[0473] inhibitors of complex II (e.g. carboxamides): benodanil,
benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram,
flutolanil, fluxapyroxad, furametpyr, isofetamid, isopyrazam,
mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane,
tecloftalam, thifluzamide,
N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide,
N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4--
carboxamide,
3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carbo-
xamide,
3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-
-4-carboxamide,
1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,
3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4--
carboxamide,
1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,
N-(7-fluoro-1,1,3-trimethylindan-4-yl)-1,3-dimethyl-pyrazole-4-carboxamid-
e,
N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-3-(difluoromethyl)--
1-methyl-pyrazole-4-carboxamide; [0474] other respiration
inhibitors (e.g. complex I, uncouplers): diflumetorim,
(5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2--
yloxy)-phenyl]ethyl}-amine; nitrophenyl derivates: binapacryl,
dinobuton, dinocap, fluazinam; ferimzone; organometal compounds:
fentin salts, such as fentin-acetate, fentin chloride or fentin
hydroxide; ametoctradin; and silthiofam;
B) Sterol Biosynthesis Inhibitors (SBI Fungicides)
[0474] [0475] C14 demethylase inhibitors (DMI fungicides):
triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole,
difenoconazole, diniconazole, diniconazole-M, epoxiconazole,
fenbuconazole, fluquinconazole, flusilazole, flutriafol,
hexaconazole, imibenconazole, ipconazole, metconazole,
myclobutanil, oxpoconazole, paclobutrazole, penconazole,
propiconazole, prothioconazole, simeconazole, tebuconazole,
tetraconazole, triadimefon, triadimenol, triticonazole,
uniconazole,
1-[rel-(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]--
5-thiocyanato-1H-[1,2,4]triazole,
2-[rel-(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]--
2H-[1,2,4]triazole-3-thiol;
2-[2-chloro-4-(4-chlorophenoxyl)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol-
,
1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-
-triazol-1-yl)ethanol,
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)b-
utan-2-ol,
2-[2-chloro-4-(4-chlorophenoxyl)phenyl]-1-(1,2,4-triazol-1-yl)b-
utan-2-ol,
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1-
,2,4-triazol-1-yl)butan-2-ol,
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)p-
ropan-2-ol,
2-[2-chloro-4-(4-chlorophenoxyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)bu-
tan-2-ol,
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triaz-
ol-1-yl)pentan-2-ol,
2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)p-
ropan-2-ol; imidazoles: imazalil, pefurazoate, prochloraz,
triflumizol; pyrimidines, pyridines and piperazines: fenarimol,
nuarimol, pyrifenox, triforine,
3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenypisoxazol-4-yl]-(3-pyrid-
yl)methanol; [0476] Delta14-reductase inhibitors: aldimorph,
dodemorph, dodemorph-acetate, fenpropimorph, tridemorph,
fenpropidin, piperalin, spiroxamine; [0477] Inhibitors of 3-keto
reductase: fenhexamid;
C) Nucleic Acid Synthesis Inhibitors
[0477] [0478] phenylamides or acyl amino acid fungicides:
benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M
(mefenoxam), ofurace, oxadixyl; [0479] others: hymexazole,
octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine,
5-fluoro-2-(ptolylmethoxy)pyrimidin-4-amine,
5-fluoro-2-(4-fluorophenylmethoxyl)pyrimidin-4-amine;
D) Inhibitors of Cell Division and Cytoskeleton
[0479] [0480] tubulin inhibitors, such as benzimidazoles,
thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole,
thiophanate-methyl; triazolopyrimidines:
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]tria-
zolo[1,5-a]pyrimidine [0481] other cell division inhibitors:
diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide,
metrafenone, pyriofenone; E) Inhibitors of amino acid and protein
synthesis [0482] methionine synthesis inhibitors
(anilino-pyrimidines): cyprodinil, mepanipyrim, pyrimethanil;
[0483] protein synthesis inhibitors: blasticidin-S, kasugamycin,
kasugamycin hydrochloridehydrate, mildiomycin, streptomycin,
oxytetracyclin, polyoxine, validamycin A;
F) Signal Transduction Inhibitors
[0483] [0484] MAP/histidine kinase inhibitors: fluoroimid,
iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
[0485] G protein inhibitors: quinoxyfen;
G) Lipid and Membrane Synthesis Inhibitors
[0486] Phospholipid biosynthesis inhibitors: edifenphos,
iprobenfos, pyrazophos, isoprothiolane; [0487] lipid peroxidation:
dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl,
chloroneb, etridiazole; [0488] phospholipid biosynthesis and cell
wall deposition: dimethomorph, flumorph, mandipropamid, pyrimorph,
benthiavalicarb, iprovalicarb, valifenalate and
N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic
acid-(4-fluorophenyl) ester; [0489] compounds affecting cell
membrane permeability and fatty acides: propamocarb,
propamocarb-hydrochlorid [0490] fatty acid amide hydrolase
inhibitors: oxathiapiprolin,
1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1--
piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone;
2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl-
)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl
methanesulfonate,
2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-y-
l)1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl
methanesulfonate; H) Inhibitors with Multi Site Action [0491]
inorganic active substances: Bordeaux mixture, copper acetate,
copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
[0492] thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,
metiram, propineb, thiram, zineb, ziram; [0493] organochlorine
compounds (e.g. phthalimides, sulfamides, chloronitriles):
anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid,
dichlorophen, hexachlorobenzene, pentachlorphenole and its salts,
phthalide, tolylfluanid,
N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
[0494] guanidines and others: guanidine, dodine, dodine free base,
guazatine, guazatineacetate, iminoctadine, iminoctadine-triacetate,
iminoctadine-tris(albesilate), dithianon,
2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-te-
traone;
I) Cell Wall Synthesis Inhibitors
[0494] [0495] inhibitors of glucan synthesis: validamycin, polyoxin
B; melanin synthesis inhibitors: pyroquilon, tricyclazole,
carpropamid, dicyclomet, fenoxanil;
J) Plant Defence Inducers
[0495] [0496] acibenzolar-S-methyl, probenazole, isotianil,
tiadinil, prohexadione-calcium; phosphonates: fosetyl,
fosetyl-aluminum, phosphorous acid and its salts;
K) Unknown Mode of Action
[0496] [0497] bronopol, chinomethionat, cyflufenamid, cymoxanil,
dazomet, debacarb, diclomezine, difenzoquat,
difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover,
flusulfamide, flutianil, methasulfocarb, nitrapyrin,
nitrothal-isopropyl, oxathiapiprolin, tolprocarb, oxin-copper,
proquinazid, tebufloquin, tecloftalam, triazoxide,
2-butoxy-6-iodo-3-propylchromen-4-one,
2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yl-
oxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]e-
thanone,
2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro--
6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl-
)piperidin-1-yl]ethanone,
bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1--
yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl-
]ethanone,
N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phe-
nyl)-methyl)-2-phenyl acetamide,
N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-
-methyl formamidine,
N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-
methyl formamidine,
N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)N-et-
hyl-N-methyl formamidine,
N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-et-
hyl-N-methyl formamidine, methoxy-acetic acid
6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester,
3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,
3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
(pyrisoxazole), N-(6-methoxy-pyridin-3-yl)cyclopropanecarboxylic
acid amide,
5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazo-
le,
2-(4-chloro-phenyl)N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-
-ynyloxy-acetamide,
ethyl(Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate, picarbutrazox,
pentyl
N-[6-[[(Z)-[(1-methyltetrazol-5-yl)phenyl-methylene]amino]oxymethyl]-2-py-
ridyl]carbamate,
2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol,
2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]-phenyl]propan-2-ol,
3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline,
3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,
3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline;
L) Biopesticides
[0497] [0498] L1) Microbial pesticides with fungicidal,
bactericidal, viricidal and/or plant defense activator activity:
Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium
pullulans, Bacillus amyloliquefaciens, B. mojavensis, B. pumilus,
B. simplex, B. solisalsi, B. subtilis, B. subtilis var.
amyloliquefaciens, Candida oleophila, C. saitoana, Clavibacter
michiganensis (bacteriophages), Coniothyrium minitans,
Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora
alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate
(also named Gliocladium catenulatum), Gliocladium roseum,
Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola,
Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus,
Paenibacillus polymyxa, Pantoea vagans, Phlebiopsis gigantea,
Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa,
Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica,
Streptomyces griseoviridis, S. lydicus, S. violaceusniger,
Talaromyces flavus, Trichoderma asperellum, T. atroviride, T.
fertile, T. gamsii, T. harmatum, T. harzianum; mixture of T.
harzianum and T. viride; mixture of T. polysporum and T. harzianum;
T. stromaticum, T. virens (also named Gliocladium virens), T.
viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium
dahlia, zucchini yellow mosaic virus (avirulent strain); [0499] L2)
Biochemical pesticides with fungicidal, bactericidal, viricidal
and/or plant defense activator activity: chitosan (hydrolysate),
harpin protein, laminarin, Menhaden fish oil, natamycin, Plum pox
virus coat protein, potassium or sodium bicarbonate, Reynoutria
sachlinensis extract, salicylic acid, tea tree oil; [0500] L3)
Microbial pesticides with insecticidal, acaricidal, molluscidal
and/or nematicidal activity: Agrobacterium radiobacter, Bacillus
cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai,
B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki,
B. t. ssp. tenebrionis, Beauveria bassiana, B. brongniartii,
Burkholderia sp., Chromobacterium subtsugae, Cydia pomonella
granulosis virus, Cryptophlebia leucotreta granulovirus (CrIeGV),
Isaria fumosorosea, Heterorhabditis bacteriophora, Lecanicillium
longisporum, L. muscarium (formerly Verticillium lecanii),
Metarhizium anisopliae, M. anisopliae var. acridum, Nomuraea
rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus
popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramose,
P. reneformis, P. thornea, P. usgae, Pseudomonas fluorescens,
Steinernema carpocapsae, S. feltiae, S. kraussei; [0501] L4)
Biochemical pesticides with insecticidal, acaricidal, molluscidal,
pheromone and/or nematicidal activity: L-carvone, citral,
(E,Z)-7,9-dodecadien-1-ylacetate, ethyl formate, (E,Z)-2,4-ethyl
decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl
butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone,
2-methyl 1-butanol, methyl eugenol, methyl jasmonate,
(E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate,
(E,Z)-3,13-octadecadien-1-ol, R-1-octen-3-ol, pentatermanone,
potassium silicate, sorbitol actanoate,
(E,Z,Z)-3,8,11-tetradecatrienyl acetate,
(Z,E)-9,12-tetradecadien-1-yl acetate, Z-7-tetradecen-2-one,
Z-9-tetradecen-1-yl acetate, Z-11-tetradecenal,
Z-11-tetradecen-1-ol, Acacia negra extract, extract of grapefruit
seeds and pulp, extract of Chenopodium ambrosiodae, Catnip oil,
Neem oil, Quillay extract, Tagetes oil; [0502] L5) Microbial
pesticides with plant stress reducing, plant growth regulator,
plant growth promoting and/or yield enhancing activity:
Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense,
A. halopraeferens, Bradyrhizobium sp., B. elkanii, B. japonicum, B.
liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices,
Mesorhizobium sp., Paenibacillus alvei, Penicillium bilaiae,
Rhizobium leguminosarum bv. phaseoli, R. I. trifolii, R. I. bv.
viciae, R. tropici, Sinorhizobium meliloti; [0503] L6) Biochemical
pesticides with plant stress reducing, plant growth regulator
and/or plant yield enhancing activity: abscisic acid, aluminium
silicate (kaolin), 3-decen-2-one, formononetin, genistein,
hesperetin, homobrassinlide, humates, jasmonic acid or salts or
derivatives thereof, lysophosphatidyl ethanolamine, naringenin,
polymeric polyhydroxy acid, Ascophyllum nodosum (Norwegian kelp,
Brown kelp) extract and Ecklonia maxima (kelp) extract;
M) Growth Regulators
[0503] [0504] abscisic acid, amidochlor, ancymidol,
6-benzylaminopurine, brassinolide, butralin, chlormequat
(chlormequat chloride), choline chloride, cyclanilide, daminozide,
dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin,
flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid,
inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide,
mepiquat (mepiquat chloride), naphthaleneacetic acid,
N-6-benzyladenine, paclobutrazol, prohexadione
(prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol,
tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid,
trinexapac-ethyl and uniconazole;
N) Herbicides
[0504] [0505] acetamides: acetochlor, alachlor, butachlor,
dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor,
metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor,
propachlor, thenylchlor; [0506] amino acid derivatives: bilanafos,
glyphosate, glufosinate, sulfosate; [0507]
aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl, fenoxaprop,
fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop,
quizalofop-P-tefuryl; [0508] Bipyridyls: diquat, paraquat; [0509]
(thio)carbamates: asulam, butylate, carbetamide, desmedipham,
dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb,
phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
[0510] cyclohexanediones: butroxydim, clethodim, cycloxydim,
profoxydim, sethoxydim, tepraloxydim, tralkoxydim; [0511]
dinitroanilines: benfluralin, ethalfluralin, oryzalin,
pendimethalin, prodiamine, trifluralin; [0512] diphenyl ethers:
acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen,
lactofen, oxyfluorfen; [0513] hydroxybenzonitriles: bomoxynil,
dichlobenil, ioxynil; [0514] imidazolinones: imazamethabenz,
imazamox, imazapic, imazapyr, imazaquin, imazethapyr; [0515]
phenoxy acetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid
(2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
[0516] pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet,
norflurazon, pyridate; [0517] pyridines: aminopyralid, clopyralid,
diflufenican, dithiopyr, fluridone, fluroxypyr, picloram,
picolinafen, thiazopyr; [0518] sulfonyl ureas: amidosulfuron,
azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron,
cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron,
flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron,
imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron,
metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron,
prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron,
sulfosulfuron, thifensulfuron, triasulfuron, tribenuron,
trifloxysulfuron, triflusulfuron, tritosulfuron,
1-((2-chloro-6-propyl-imidazo[1,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimet-
hoxy-pyrimidin-2-yl)urea; [0519] triazines: ametryn, atrazine,
cyanazine, dimethametryn, ethiozin, hexazinone, metamitron,
metribuzin, prometryn, simazine, terbuthylazine, terbutryn,
triaziflam; [0520] ureas: chlorotoluron, daimuron, diuron,
fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;
[0521] other acetolactate synthase inhibitors: bispyribac-sodium,
cloransulam-methyl, diclosulam, florasulam, flucarbazone,
flumetsulam, metosulam, ortho-sulfamuron, penoxsulam,
propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid,
pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone,
pyroxsulam; [0522] others: amicarbazone, aminotriazole, anilofos,
beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap,
bentazone, benzobicyclon, bicyclopyrone, bromacil, bromobutide,
butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl,
chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide,
dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras,
endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide,
flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone,
flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil,
propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic
acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone,
pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotole,
pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione,
sulfentrazone, terbacil, tefuryltrione, tembotrione,
thiencarbazone, topramezone,
(3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-
-2H-pyrimidin-1-yl)-phenoxy]-pyridin-2-yloxy)-acetic acid ethyl
ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidine-4-carboxylic acid
methyl ester,
6-chloro-3-(2-cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol,
4-amino-3-chloro-6-(4-chloro-phenyl)-5-fluoro-pyridine-2-carboxylic
acid,
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-pyridine-2-carboxy-
lic acid methyl ester, and
4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)-pyridine-2--
carboxylic acid methyl ester.
O) Insecticides
[0522] [0523] organo(thio)phosphates: acephate, azamethiphos,
azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl,
chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate,
disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion,
methamidophos, methidathion, methyl-parathion, mevinphos,
monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate,
phosalone, phosmet, phosphamidon, phorate, phoxim,
pirimiphos-methyl, profenofos, prothiofos, sulprophos,
tetrachlorvinphos, terbufos, triazophos, trichlorfon; [0524]
carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl,
carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb,
methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
[0525] pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin,
cyphenothrin, cypermethrin, alphacypermethrin, beta-cypermethrin,
zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox,
fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin,
permethrin, prallethrin, pyrethrin I and II, resmethrin,
silafluofen, tau-fluvalinate, tefluthrin, tetramethrin,
tralomethrin, transfluthrin, profluthrin, dimefluthrin; [0526]
insect growth regulators: a) chitin synthesis inhibitors:
benzoylureas: chlorfluazuron, cyramazin, diflubenzuron,
flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,
teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox,
etoxazole, clofentazine; b) ecdysone antagonists: halofenozide,
methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids:
pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis
inhibitors: spirodiclofen, spiromesifen, spirotetramat; [0527]
nicotinic receptor agonists/antagonists compounds: clothianidin,
dinotefuran, flupyradifurone, imidacloprid, thiamethoxam,
nitenpyram, acetamiprid, thiacloprid,
1-2-chlorothiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1,3,5]triazinane;
[0528] GABA antagonist compounds: endosulfan, ethiprole, fipronil,
vaniliprole, pyrafluprole, pyriprole,
5-amino-1-(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl-1H-pyrazole-3-carb-
othioic acid amide; [0529] macrocyclic lactone insecticides:
abamectin, emamectin, milbemectin, lepimectin, spinosad,
spinetoram; [0530] mitochondrial electron transport inhibitor
(METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad,
tolfenpyrad, flufenerim; [0531] METI II and III compounds:
acequinocyl, fluacyprim, hydramethylnon; [0532] Uncouplers:
chlorfenapyr; [0533] oxidative phosphorylation inhibitors:
cyhexatin, diafenthiuron, fenbutatin oxide, propargite; moulting
disruptor compounds: cryomazine; [0534] mixed function oxidase
inhibitors: piperonyl butoxide; [0535] sodium channel blockers:
indoxacarb, metaflumizone; [0536] ryanodine receptor inhibitors:
chlorantraniliprole, cyantraniliprole, flubendiamide,
N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(-
3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl-
]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-ph-
enyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-
-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(-
3-chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide;
N-[4,6-dibromo-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]--
2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phe-
nyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-
-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide);
[0537] others: benclothiaz, bifenazate, cartap, flonicamid,
pyridalyl, pymetrozine, sulfur, thiocyclam, cyenopyrafen,
flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron,
pyrifluquinazon and
1,1'-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]methy-
l]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-11-o-
xo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl]cyclop-
ropaneacetic acid ester.
[0538] The present invention furthermore relates to compositions
comprising a compound I (component 1) and at least one further
active substance useful for plant protection, e.g. selected from
the groups A) to O) (component 2), in particular one further
fungicide, e.g. fungicide from the groups A) to K), as described
above, and if desired one suitable solvent or solid carrier. Those
compositions are of particular interest, since many of them at the
same application rate show higher efficiencies against harmful
fungi. Furthermore, combating harmful fungi with a compristion
comprising a compound I and a fungicide from groups A) to K), as
described above, is more efficient than combating those fungi with
individual compounds I or individual fungicides from groups A) to
K). By applying compounds I together with at least one active
substance from groups A) to O) a synergistic effect can be
obtained, i.e. more then simple addition of the individual effects
is obtained (synergistic compositions).
[0539] This can be obtained by applying the compounds I and at
least one further active substance simultaneously, either jointly
(e.g. as tank-mix) or seperately, or in succession, wherein the
time interval between the individual applications is selected to
ensure that the active substance applied first still occurs at the
site of action in a sufficient amount at the time of application of
the further active substance(s). The order of application is not
essential for working of the present invention.
[0540] When applying a compound of the present invention and a
pesticide II sequentially the time between both applications may
vary e.g. between 2 hours to 7 days. Also a broader range is
possible ranging from 0.25 hour to 30 days, preferably from 0.5
hour to 14 days, particularly from 1 hour to 7 days or from 1.5
hours to 5 days, even more preferred from 2 hours to 1 day. In case
of a composition or mixture comprising a pesticide II selected from
group L), it is preferred that the pesticide II is applied as last
treatment.
[0541] According to the invention, the solid material (dry matter)
of the biopesticides (with the exception of oils such as Neem oil,
Tagetes oil, etc.) are considered as active components (e.g. to be
obtained after drying or evaporation of the extraction medium or
the suspension medium in case of liquid formulations of the
microbial pesticides).
[0542] In accordance with the present invention, the weight ratios
and percentages used herein for a biological extract such as
Quillay extract are based on the total weight of the dry content
(solid material) of the respective extract(s).
[0543] The total weight ratios of compositions comprising at least
one microbial pesticide in the form of viable microbial cells
including dormant forms, can be determined using the amount of CFU
of the respective microorganism to calculate the total weight of
the respective active component with the following equation that
1.times.10.sup.9 CFU equals one gram of total weight of the
respective active component. Colony forming unit is measure of
viable microbial cells, in particular fungal and bacterial cells.
In addition, here "CFU" may also be understood as the number of
(juvenile) individual nematodes in case of (entomopathogenic)
nematode biopesticides, such as Steinernema feltiae.
[0544] In the binary mixtures and compositions according to the
invention the weight ratio of the component 1) and the component 2)
generally depends from the properties of the active components
used, usually it is in the range of from 1:100 to 100:1, regularly
in the range of from 1:50 to 50:1, preferably in the range of from
1:20 to 20:1, more preferably in the range of from 1:10 to 10:1,
even more preferably in the range of from 1:4 to 4:1 and in
particular in the range of from 1:2 to 2:1.
[0545] According to a further embodiments of the binary mixtures
and compositions, the weight ratio of the component 1) and the
component 2) usually is in the range of from 1000:1 to 1:1, often
in the range of from 100:1 to 1:1, regularly in the range of from
50:1 to 1:1, preferably in the range of from 20:1 to 1:1, more
preferably in the range of from 10:1 to 1:1, even more preferably
in the range of from 4:1 to 1:1 and in particular in the range of
from 2:1 to 1:1.
[0546] According to a further embodiments of the binary mixtures
and compositions, the weight ratio of the component 1) and the
component 2) usually is in the range of from 1:1 to 1:1000, often
in the range of from 1:1 to 1:100, regularly in the range of from
1:1 to 1:50, preferably in the range of from 1:1 to 1:20, more
preferably in the range of from 1:1 to 1:10, even more preferably
in the range of from 1:1 to 1:4 and in particular in the range of
from 1:1 to 1:2.
[0547] In the ternary mixtures, i.e. compositions according to the
invention comprising the component 1) and component 2) and a
compound III (component 3), the weight ratio of component 1) and
component 2) depends from the properties of the active substances
used, usually it is in the range of from 1:100 to 100:1, regularly
in the range of from 1:50 to 50:1, preferably in the range of from
1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and
in particular in the range of from 1:4 to 4:1, and the weight ratio
of component 1) and component 3) usually it is in the range of from
1:100 to 100:1, regularly in the range of from 1:50 to 50:1,
preferably in the range of from 1:20 to 20:1, more preferably in
the range of from 1:10 to 10:1 and in particular in the range of
from 1:4 to 4:1.
[0548] Any further active components are, if desired, added in a
ratio of from 20:1 to 1:20 to the component 1).
[0549] These ratios are also suitable for inventive mixtures
applied by seed treatment.
[0550] In compositions according to the invention comprising one
compound I (component 1) and one further pesticidally active
substance (component 2), e.g. one active substance from groups A)
to K), the weight ratio of component 1 and component 2 generally
depends from the properties of the active substances used, usually
it is in the range of from 1:100 to 100:1, regularly in the range
of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1,
more preferably in the range of from 1:10 to 10:1 and in particular
in the range of from 1:3 to 3:1.
[0551] In compositions according to the invention comprising one
compound I (component 1) and a first further pesticidally active
substance (component 2) and a second further pesticidally active
substance (component 3), e.g. two active substances from groups A)
to K), the weight ratio of component 1 and component 2 depends from
the properties of the active substances used, preferably it is in
the range of from 1:50 to 50:1 and particularly in the range of
from 1:10 to 10:1, and the weight ratio of component 1 and
component 3 preferably is in the range of from 1:50 to 50:1 and
particularly in the range of from 1:10 to 10:1.
[0552] Preference is also given to compositions comprising a
compound I (component 1) and at least one active substance selected
from group A) (component 2) and particularly selected from
azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl,
orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin;
famoxadone, fenamidone; benzovindiflupyr, bixafen, boscalid,
fluopyram, fluxapyroxad, isopyrazam, penflufen, penthiopyrad,
sedaxane; ametoctradin, cyazofamid, fluazinam, fentin salts, such
as fentin acetate.
[0553] Preference is given to compositions comprising a compound of
formula I (component 1) and at least one active substance selected
from group B) (component 2) and particularly selected from
cyproconazole, difenoconazole, epoxiconazole, fluquinconazole,
flusilazole, flutriafol, metconazole, myclobutanil, penconazole,
propiconazole, prothioconazole, triadimefon, triadimenol,
tebuconazole, tetraconazole, triticonazole, prochloraz, fenarimol,
triforine; dodemorph, fenpropimorph, tridemorph, fenpropidin,
spiroxamine; fenhexamid.
[0554] Preference is given to compositions comprising a compound of
formula I (component 1) and at least one active substance selected
from group C) (component 2) and particularly selected from
metalaxyl, (metalaxyl-M) mefenoxam, ofurace.
[0555] Preference is given to compositions comprising a compound of
formula I (component 1) and at least one active substance selected
from group D) (component 2) and particularly selected from benomyl,
carbendazim, thiophanate-methyl, ethaboxam, fluopicolide, zoxamide,
metrafenone, pyriofenone.
[0556] Preference is also given to compositions comprising a
compound I (component 1) and at least one active substance selected
from group E) (component 2) and particularly selected from
cyprodinil, mepanipyrim, pyrimethanil.
[0557] Preference is also given to compositions comprising a
compound I (component 1) and at least one active substance selected
from group F) (component 2) and particularly selected from
iprodione, fludioxonil, vinclozolin, quinoxyfen.
[0558] Preference is also given to compositions comprising a
compound I (component 1) and at least one active substance selected
from group G) (component 2) and particularly selected from
dimethomorph, flumorph, iprovalicarb, benthiavalicarb,
mandipropamid, propamocarb.
[0559] Preference is also given to compositions comprising a
compound I (component 1) and at least one active substance selected
from group H) (component 2) and particularly selected from copper
acetate, copper hydroxide, copper oxychloride, copper sulfate,
sulfur, mancozeb, metiram, propineb, thiram, captafol, folpet,
chlorothalonil, dichlofluanid, dithianon.
[0560] Preference is also given to compositions comprising a
compound I (component 1) and at least one active substance selected
from group I) (component 2) and particularly selected from
carpropamid and fenoxanil.
[0561] Preference is also given to compositions comprising a
compound I (component 1) and at least one active substance selected
from group J) (component 2) and particularly selected from
acibenzolar-S-methyl, probenazole, tiadinil, fosetyl,
fosetyl-aluminium, H.sub.3PO.sub.3 and salts thereof.
[0562] Preference is also given to compositions comprising a
compound I (component 1) and at least one active substance selected
from group K) (component 2) and particularly selected from
cymoxanil, proquinazid and
N-methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piper-
idin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamid-
e.
[0563] The biopesticides from group L) of pesticides II, their
preparation and their pesticidal activity e.g. against harmful
fungi or insects are known (e-Pesticide Manual V 5.2 (ISBN 978 1
901396 85 0) (2008-2011);
http://www.epa.gov/opp00001/biopesticides/, see product lists
therein; http://www.omri.org/omri-lists, see lists therein;
Bio-Pesticides Database BPDB http://sitem.herts.ac.uk/aeru/bpdb/,
see A to Z link therein).
[0564] The biopesticides from group L1) and/or L2) may also have
insecticidal, acaricidal, molluscidal, pheromone, nematicidal,
plant stress reducing, plant growth regulator, plant growth
promoting and/or yield enhancing activity. The biopesticides from
group L3) and/or L4) may also have fungicidal, bactericidal,
viricidal, plant defense activator, plant stress reducing, plant
growth regulator, plant growth promoting and/or yield enhancing
activity. The biopesticides from group L5) and/or L6) may also have
fungicidal, bactericidal, viricidal, plant defense activator,
insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal
activity.
[0565] Many of these biopesticides are registered and/or are
commercially available: aluminium silicate (Screen.TM. Duo from
Certis LLC, USA), Agrobacterium radiobacter K1026 (e.g. NoGall.RTM.
from Becker Underwood Pty Ltd., Australia), A. radiobacter K84
(Nature 280, 697-699, 1979; e.g. GallTroll.RTM. from AG Biochem,
Inc., C, USA), Ampelomyces quisqualis M-10 (e.g. AQ 10.RTM. from
Intrachem Bio GmbH & Co. KG, Germany), Ascophyllum nodosum
(Norwegian kelp, Brown kelp) extract or filtrate (e.g. ORKA GOLD
from Becker Underwood, South Africa; or Goemar.RTM. from
Laboratoires Goemar, France), Aspergillus flavus NRRL 21882
isolated from a peanut in Georgia in 1991 by the USDA, National
Peanut Research Laboratory (e.g. in Afla-Guard.RTM. from Syngenta,
CH), mixtures of Aureobasidium pullulans DSM14940 and DSM 14941
(e.g. blastospores in BlossomProtect.RTM. from bio-ferm GmbH,
Germany), Azospirillum amazonense BR 11140 (SpY2T) (Proc. 9.sup.th
Int. and 1.sup.st Latin American PGPR meeting, Quimara, Medellin,
Colombia 2012, p. 60, ISBN 978-958-46-0908-3), A. brasilense AZ39
(Eur. J. Soil Biol 45(1), 28-35, 2009), A. brasilense XOH (e.g.
AZOS from Xtreme Gardening, USA or RTI Reforestation Technologies
International; USA), A. brasilense BR 11002 (Proc. 9.sup.th Int.
and 1.sup.st Latin American PGPR meeting, Quimara, Medellin,
Colombia 2012, p. 60, ISBN 978-958-46-0908-3), A. brasilense BR
11005 (SP245; e.g. in GELFIX Gramineas from BASF Agricultural
Specialties Ltd., Brazil), A. lipoferum BR 11646 (Sp31) (Proc.
9.sup.th Int. and 1.sup.st Latin American PGPR meeting, Quimara,
Medellin, Colombia 2012, p. 60), Bacillus amyloliquefaciens FZB42
(e.g. in RhizoVital.RTM. 42 from AbiTEP GmbH, Berlin, Germany), B.
amyloliquefaciens IN937a (J. Microbiol. Biotechnol. 17(2), 280-286,
2007; e.g. in BioYield.RTM. from Gustafson LLC, TX, USA), B.
amyloliquefaciens IT-45 (CNCM 1-3800) (e.g. Rhizocell C from ITHEC,
France), B. amyloliquefaciens subsp. plantarum MBI600 (NRRL
B-50595, deposited at United States Department of Agriculture)
(e.g. Integral.RTM., Subtilex.RTM. NG from Becker Underwood, USA),
B. cereus CNCM 1-1562 (U.S. Pat. No. 6,406,690), B. firmus CNCM
1-1582 (WO 2009/126473, WO 2009/124707, U.S. Pat. No. 6,406,690;
Votivo.RTM. from Bayer Crop Science LP, USA), B. pumilus GB34 (ATCC
700814; e.g. in YieldShield.RTM. from Gustafson LLC, TX, USA), and
Bacillus pumilus KFP9F (NRRL B-50754) (e.g. in BAC-UP or FUSION-P
from Becker Underwood South Africa), B. pumilus QST 2808 (NRRL
B-30087) (e.g. Sonata.RTM. and Ballad.RTM. Plus from AgraQuest
Inc., USA), B. subtilis GB03 (e.g. Kodiak.RTM. or BioYield.RTM.
from Gustafson, Inc., USA; or Companion.RTM. from Growth Products,
Ltd., White Plains, N.Y. 10603, USA), B. subtilis GB07 (Epic.RTM.
from Gustafson, Inc., USA), B. subtilis QST-713 (NRRL B-21661 in
Rhapsody.RTM., Serenade.RTM. MAX and Serenade.RTM. ASO from
AgraQuest Inc., USA), B. subtilis var. amyloliquefaciens FZB24
(e.g. Taegro.RTM. from Novozyme Biologicals, Inc., USA), B.
subtilis var. amyloliquefaciens D747 (e.g. Double Nickel 55 from
Certis LLC, USA), B. thuringiensis ssp. aizawai ABTS-1857 (e.g. in
XenTari.RTM. from BioFa AG, Munsingen, Germany), B. t. ssp. aizawai
SAN 401 I, ABG-6305 and ABG-6346, Bacillus t. ssp. israelensis
AM65-52 (e.g. in VectoBac.RTM. from Valent BioSciences, IL, USA),
Bacillus thuringiensis ssp. kurstaki SB4 (NRRL B-50753; e.g. Beta
Pro.RTM. from Becker Underwood, South Africa), B. t. ssp. kurstaki
ABTS-351 identical to HD-1 (ATCC SD-1275; e.g. in Dipel.RTM. DF
from Valent BioSciences, IL, USA), B. t. ssp. kurstaki EG 2348
(e.g. in Lepinox.RTM. or Rapax.RTM. from CBC (Europe) S.r.I.,
Italy), B. t. ssp. tenebrionis DSM 2803 (EP 0 585 215 B1; identical
to NRRL B-15939; Mycogen Corp.), B. t. ssp. tenebrionis NB-125 (DSM
5526; EP 0 585 215 B1; also referred to as SAN 418 I or ABG-6479;
former production strain of Novo-Nordisk), B. t. ssp. tenebrionis
NB-176 (or NB-176-1) a gamma-irridated, induced high-yielding
mutant of strain NB-125 (DSM 5480; EP 585 215 B1; Novodor.RTM. from
Valent BioSciences, Switzerland), Beauveria bassiana ATCC 74040
(e.g. in Naturalis.RTM. from CBC (Europe) S.r.I., Italy), B.
bassiana DSM 12256 (US 200020031495; e.g. BioExpert.RTM. SC from
Live Sytems Technology S.A., Colombia), B. bassiana GHA
(BotaniGard.RTM. 22WGP from Laverlam Int. Corp., USA), B. bassiana
PPRI 5339 (ARSEF number 5339 in the USDA ARS collection of
entomopathogenic fungal cultures; NRRL 50757) (e.g. BroadBand.RTM.
from Becker Underwood, South Africa), B. brongniartii (e.g. in
Melocont.RTM. from Agrifutur, Agrianello, Italy, for control of
cockchafer; J. Appl. Microbiol. 100(5),1063-72, 2006),
Bradyrhizobium sp. (e.g. Vault.RTM. from Becker Underwood, USA), B.
japonicum (e.g. VAULT.RTM. from Becker Underwood, USA), Candida
oleophila 1-182 (NRRL Y-18846; e.g. Aspire.RTM. from Ecogen Inc.,
USA, Phytoparasitica 23(3), 231-234, 1995), C. oleophila strain O
(NRRL Y-2317; Biological Control 51, 403-408, 2009), Candida
saitoana (e.g. Biocure.RTM. (in mixture with lysozyme) and
BioCoat.RTM. from Micro Flo Company, USA (BASF SE) and Arysta),
Chitosan (e.g. ArmourZen.RTM. from BotriZen Ltd., NZ), Clonostachys
rosea f. catenulata, also named Gliocladium catenulatum (e.g.
isolate J 1446: Prestop.RTM. from Verdera Oy, Finland),
Chromobacterium subtsugae PRAA4-1 isolated from soil under an
eastern hemlock (Tsuga canadensis) in the Catoctin Mountain region
of central Maryland (e.g. in GRANDEVO from Marrone Bio Innovations,
USA), Coniothyrium minitans CON/M/91-08 (e.g. Contans.RTM. WG from
Prophyta, Germany), Cryphonectria parasitica (e.g. Endothia
parasitica from CNICM, France), Cryptococcus albidus (e.g. YIELD
PLUS.RTM. from Anchor Bio-Technologies, South Africa),
Cryptophlebia leucotreta granulovirus (CrIeGV) (e.g. in CRYPTEX
from Adermatt Biocontrol, Switzerland), Cydia pomonella
granulovirus (CpGV) V03 (DSM GV-0006; e.g. in MADEX Max from
Andermatt Biocontrol, Switzerland), CpGV V22 (DSM GV-0014; e.g. in
MADEX Twin from Adermatt Biocontrol, Switzerland), Delftia
acidovorans RAY209 (ATCC PTA-4249; WO 2003/57861; e.g. in BIOBOOST
from Brett Young, Winnipeg, Canada), Dilophosphora alopecuri (Twist
Fungus from Becker Underwood, Australia), Ecklonia maxima (kelp)
extract (e.g. KELPAK SL from Kelp Products Ltd, South Africa),
formononetin (e.g. in MYCONATE from Plant Health Care plc, U.K.),
Fusarium oxysporum (e.g. BIOFOX.RTM. from S.I.A.P.A., Italy,
FUSACLEAN.RTM. from Natural Plant Protection, France), Glomus
intraradices (e.g. MYC 4000 from ITHEC, France), Glomus
intraradices RTI-801 (e.g. MYKOS from Xtreme Gardening, USA or RTI
Reforestation Technologies International; USA), grapefruit seeds
and pulp extract (e.g. BC-1000 from Chemie S.A., Chile), harpin
(alpha-beta) protein (e.g. MESSENGER or HARP--N-Tek from Plant
Health Care plc, U.K.; Science 257, 1-132, 1992), Heterorhabditis
bacteriophaga (e.g. Nemasys.RTM. G from Becker Underwood Ltd., UK),
Isaria fumosorosea Apopka-97 (ATCC 20874) (PFR-97.TM. from Certis
LLC, USA), cis-jasmone (U.S. Pat. No. 8,221,736), laminarin (e.g.
in VACCIPLANT from Laboratoires Goemar, St. Malo, France or Stahler
SA, Switzerland), Lecanicillium longisporum KV42 and KV71 (e.g.
VERTALEC.RTM. from Koppert BV, Netherlands), L. muscarium KV01
(formerly Verticillium lecanii) (e.g. MYCOTAL from Koppert BV,
Netherlands), Lysobacter antibioticus 13-1 (Biological Control 45,
288-296, 2008), L. antibioticus HS124 (Curr. Microbiol. 59(6),
608-615, 2009), L. enzymogenes 3.1T8 (Microbiol. Res. 158, 107-115;
Biological Control 31(2), 145-154, 2004), Metarhizium anisopliae
var. acridum IMI 330189 (isolated from Ornithacris cavroisi in
Niger; also NRRL 50758) (e.g. GREEN MUSCLE.RTM. from Becker
Underwood, South Africa), M. a. var. acridum FI-985 (e.g. GREEN
GUARD.RTM. SC from Becker Underwood Pty Ltd, Australia), M.
anisopliae FI-1045 (e.g. BIOCANE.RTM. from Becker Underwood Pty
Ltd, Australia), M. anisopliae F52 (DSM 3884, ATCC 90448; e.g.
MET52.RTM. Novozymes Biologicals BioAg Group, Canada), M.
anisopliae ICIPE 69 (e.g. METATHRIPOL from ICIPE, Nairobe, Kenya),
Metschnikowia fructicola (NRRL Y-30752; e.g. SHEMER.RTM. from
Agrogreen, Israel, now distributed by Bayer CropSciences, Germany;
U.S. Pat. No. 6,994,849), Microdochium dimerum (e.g. ANTIBOT.RTM.
from Agrauxine, France), Microsphaeropsis ochracea P130A (ATCC
74412 isolated from apple leaves from an abandoned orchard,
St-Joseph-du-Lac, Quebec, Canada in 1993; Mycologia 94(2), 297-301,
2002), Muscodor albus QST 20799 originally isolated from the bark
of a cinnamon tree in Honduras (e.g. in development products
Muscudor.TM. or QRD300 from AgraQuest, USA), Neem oil (e.g.
TRILOGY.RTM., TRIACT.RTM. 70 EC from Certis LLC, USA), Nomuraea
rileyi strains SA86101, GU87401, SR86151, CG128 and VA9101,
Paecilomyces fumosoroseus FE 9901 (e.g. NO FLY.TM. from Natural
Industries, Inc., USA), P. lilacinus 251 (e.g. in
BioAct.RTM./MeloCon.RTM. from Prophyta, Germany; Crop Protection
27, 352-361, 2008; originally isolated from infected nematode eggs
in the Philippines), P. lilacinus DSM 15169 (e.g. NEMATA.RTM. SC
from Live Systems Technology S.A., Colombia), P. lilacinus BCP2
(NRRL 50756; e.g. PL GOLD from Becker Underwood BioAg SA Ltd, South
Africa), mixture of Paenibacillus alvei NAS6G6 (NRRL B-50755),
Pantoea vagans (formerly agglomerans) C.sub.9-1 (originally
isolated in 1994 from apple stem tissue; BlightBan C9-1.RTM. from
NuFrams America Inc., USA, for control of fire blight in apple; J.
Bacteriol. 192(24) 6486-6487, 2010), Pasteuria spp. ATCC PTA-9643
(WO 2010/085795), Pasteuria spp. ATCC SD-5832 (WO 2012/064527), P.
nishizawae (WO 2010/80169), P. penetrans (U.S. Pat. No. 5,248,500),
P. ramose (WO 2010/80619), P. thornea (WO 2010/80169), P. usgae (WO
2010/80169), Penicillium bilaiae (e.g. Jump Start.RTM. from
Novozymes Biologicals BioAg Group, Canada, originally isolated from
soil in southern Alberta; Fertilizer Res. 39, 97-103, 1994),
Phlebiopsis gigantea (e.g. RotStop.RTM. from Verdera Oy, Finland),
Pichia anomala WRL-076 (NRRL Y-30842; U.S. Pat. No. 8,206,972),
potassium bicarbonate (e.g. Amicarb.RTM. fromm Stahler SA,
Switzerland), potassium silicate (e.g. Sil-MATRIX.TM. from Certis
LLC, USA), Pseudozyma flocculosa PF-A22 UL (e.g. Sporodex.RTM. from
Plant Products Co. Ltd., Canada), Pseudomonas sp. DSM 13134 (WO
2001/40441, e.g. in PRORADIX from Sourcon Padena GmbH & Co. KG,
Hechinger Str. 262, 72072 Tubingen, Germany), P. chloraphis MA 342
(e.g. in CERALL or CEDEMON from BioAgri AB, Uppsala, Sweden), P.
fluorescens CL 145A (e.g. in ZEQUANOX from Marrone BioInnovations,
Davis, Calif., USA; J. Invertebr. Pathol. 113(1):104-14, 2013),
Pythium oligandrum DV 74 (ATCC 38472; e.g. POLYVERSUM.RTM. from
Remeslo SSRO, Biopreparaty, Czech Rep. and GOWAN, USA; US
2013/0035230), Reynoutria sachlinensis extract (e.g. REGALIA.RTM.
SC from Marrone Biolnnovations, Davis, Calif., USA), Rhizobium
leguminosarum bv. phaseoli (e.g. RHIZO-STICK from Becker Underwood,
USA), R. I. trifolii RP113-7 (e.g. DORMAL from Becker Underwood,
USA; Appl. Environ. Microbiol. 44(5), 1096-1101), R. I. bv. viciae
P1NP3Cst (also referred to as 1435; New Phytol 179(1), 224-235,
2008; e.g. in NODULATOR PL Peat Granule from Becker Underwood, USA;
or in NODULATOR XL PL bfrom Becker Underwood, Canada), R. I. bv.
viciae SU303 (e.g. NODULAID Group E from Becker Underwood,
Australia), R. I. bv. viciae WSM1455 (e.g. NODULAID Group F from
Becker Underwood, Australia), R. tropici SEMIA 4080 (identical to
PRF 81; Soil Biology & Biochemistry 39, 867-876, 2007),
Sinorhizobium meliloti MSDJ0848 (INRA, France) also referred to as
strain 2011 or RCR2011 (Mol Gen Genomics (2004) 272: 1-17; e.g.
DORMAL ALFALFA from Becker Underwood, USA; NITRAGINO Gold from
Novozymes Biologicals BioAg Group, Canada), Sphaerodes
mycoparasitica IDAC 301008-01 (WO 2011/022809), Steinernema
carpocapsae (e.g. MILLENIUMO from Becker Underwood Ltd., UK), S.
feltiae (NEMASHIELDO from BioWorks, Inc., USA; NEMASYSO from Becker
Underwood Ltd., UK), S. kraussei L137 (NEMASYSO L from Becker
Underwood Ltd., UK), Streptomyces griseoviridis K61 (e.g. MYCOSTOPO
from Verdera Oy, Espoo, Finland; Crop Protection 25, 468-475,
2006), S. lydicus WYEC 108 (e.g. Actinovate0 from Natural
Industries, Inc., USA, U.S. Pat. No. 5,403,584), S. violaceusniger
YCED-9 (e.g. DT-9.RTM. from Natural Industries, Inc., USA, U.S.
Pat. No. 5,968,503), Talaromyces flavus V117b (e.g. PROTUSO from
Prophyta, Germany), Trichoderma asperellum SKT-1 (e.g.
ECO-HOPE.RTM. from Kumiai Chemical Industry Co., Ltd., Japan), T.
asperellum ICC012 (e.g. in TENET WP, REMDIER WP, BIOTEN WP from
Isagro N.C., USA, BIO-TAM from AgraQuest, USA), T. atroviride LC52
(e.g. SENTINEL.RTM. from Agrimm Technologies Ltd, NZ), T.
atroviride CNCM 1-1237 (e.g. in Esquive WG from Agrauxine S.A.,
France, e.g. against pruning wound diseases on vine and plant root
pathogens), T. fertile JM41 R (NRRL 50759; e.g. RICHPLUS.TM. from
Becker Underwood Bio Ag SA Ltd, South Africa), T. gamsii ICC080
(e.g. in TENET WP, REMDIER WP, BIOTEN WP from Isagro N.C., USA,
BIO-TAM from AgraQuest, USA), T. harzianum T-22 (e.g. PLANTSHIELDO
der Firma BioWorks Inc., USA), T. harzianum TH 35 (e.g. ROOT
PRO.RTM. from Mycontrol Ltd., Israel), T. harzianum T-39 (e.g.
TRICHODEXO and TRICHODERMA 2000.RTM. from Mycontrol Ltd., Israel
and Makhteshim Ltd., Israel), T. harzianum and T. viride (e.g.
TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012
and T. viride ICC080 (e.g. REMEDIERO WP from Isagro Ricerca,
Italy), T. polysporum and T. harzianum (e.g. BINABO from BINAB
BioInnovation AB, Sweden), T. stromaticum (e.g. TRICOVABO from
C.E.P.L.A.C., Brazil), T. virens GL-21 (also named Gliocladium
virens) (e.g. SOILGARDO from Certis LLC, USA), T. viride (e.g.
TRIECO.RTM. from Ecosense Labs. (India) Pvt. Ltd., Indien,
BIO-CURE.RTM. F from T. Stanes & Co. Ltd., Indien), T. viride
TV1 (e.g. T. viride TV1 from Agribiotec srl, Italy) and Ulocladium
oudemansii HRU3 (e.g. in BOTRY-ZEN.RTM. from Botry-Zen Ltd,
NZ).
[0566] Strains can be sourced from genetic resource and deposition
centers: American Type Culture Collection, 10801 University Blvd.,
Manassas, Va. 20110-2209, USA (strains with ATCC prefic); CABI
Europe--International Mycological Institute, Bakeham Lane, Egham,
Surrey, TW20 9TYNRRL, UK (strains with prefices CABI and IMI);
Centraalbureau voor Schimmelcultures, Fungal Biodiversity Centre,
Uppsalaan 8, PO Box 85167, 3508 AD Utrecht, Netherlands (strains
with prefic CBS); Division of Plant Industry, CSIRO, Canberra,
Australia (strains with prefix CC); Collection Nationale de
Cultures de Microorganismes, Institut Pasteur, 25 rue du Docteur
Roux, F-75724 PARIS Cedex 15 (strains with prefix CNCM);
Leibniz-Institut DSMZ-Deutsche Sammlung von Mikroorganismen and
Zellkulturen GmbH, Inhoffenstra.beta.e 7 B, 38124 Braunschweig,
Germany (strains with prefix DSM); International Depositary
Authority of Canada Collection, Canada (strains with prefix IDAC);
Interntional Collection of Micro-orgniasms from Plants, Landcare
Research, Private Bag 92170, Auckland Mail Centre, Auckland 1142,
New Zealand (strans with prefix ICMP); IITA, PMB 5320, Ibadan,
Nigeria (straisn with prefix IITA); The National Collections of
Industrial and Marine Bacteria Ltd., Torry Research Station, P.O.
Box 31, 135 Abbey Road, Aberdeen, AB9 8DG, Scotland (strains with
prefix NCIMB); ARS Culture Collection of the National Center for
Agricultural Utilization Research, Agricultural Research Service,
U.S. Department of Agriculture, 1815 North University Street,
Peoria, Ill. 61604, USA (strains with prefix NRRL); Department of
Scientific and Industrial Research Culture Collection, Applied
Biochemistry Division, Palmerston North, New Zealand (strains with
prefix NZP); FEPAGRO-Fundaao Estadual de Pesquisa Agropecuaria, Rua
Gonsalves Dias, 570, Bairro Menino Deus, Porto Alegre/RS, Brazil
(strains with prefix SEMIA); SARDI, Adelaide, South Australia
(strains with prefix SRDI); U.S. Department of Agriculture,
Agricultural Research Service, Soybean and Alfalfa Research
Laboratory, BARC-West, 10300 Baltimore Boulevard, Building 011,
Room 19-9, Beltsville, Md. 20705, USA (strains with prefix USDA:
Beltsville Rhizobium Culture Collection Catalog March 1987 USDA-ARS
ARS-30:
http://pdf.usaid.gov/pdf_docs/PNAAW891.pdf); and Murdoch
University, Perth, Western Australia (strains with prefix WSM).
Further strains may be found at the Global catalogue of
Microorganisms: http://gcm.wfcc.info/ and
http://www.landcareresearch.co.nz/resources/collections/icmp and
further references to strain collections and their prefixes at
http://refs.wdcm.org/collections.htm.
[0567] Bacillus amyloliquefaciens subsp. plantarum MBI600 (NRRL
B-50595) is deposited under accession number NRRL B-50595 with the
strain designation Bacillus subtilis 1430 (and identical to NCIMB
1237). Recently, MBI 600 has been re-classified as Bacillus
amyloliquefaciens subsp. plantarum based on polyphasic testing
which combines classical microbiological methods relying on a
mixture of traditional tools (such as culture-based methods) and
molecular tools (such as genotyping and fatty acids analysis).
Thus, Bacillus subtilis MBI600 (or MBI 600 or MBI-600) is identical
to Bacillus amyloliquefaciens subsp. plantarum MBI600, formerly
Bacillus subtilis MBI600. Bacillus amyloliquefaciens MBI600 is
known as plant growth-promoting rice seed treatment from Int. J.
Microbiol. Res. 3(2) (2011), 120-130 and further described e.g. in
US 2012/0149571 A1. This strain MBI600 is e.g. commercially
available as liquid formulation product INTEGRAL.RTM.
(Becker-Underwood Inc., USA).
[0568] Bacillus subtilis strain FB17 was originally isolated from
red beet roots in North America (System Appl. Microbiol 27 (2004)
372-379). This B. subtilis strain promotes plant health (US
2010/0260735 A1; WO 2011/109395 A2). B. subtilis FB17 has also been
deposited at ATCC under number PTA-11857 on Apr. 26, 2011. Bacillus
subtilis strain FB17 may be referred elsewhere to as UD1022 or
UD10-22.
[0569] Bacillus amyloliquefaciens AP-136 (NRRL B-50614), B.
amyloliquefaciens AP-188 (NRRL B-50615), B. amyloliquefaciens
AP-218 (NRRL B-50618), B. amyloliquefaciens AP-219 (NRRL B-50619),
B. amyloliquefaciens AP-295 (NRRL B-50620), B. japonicum SEMIA 5079
(e.g. Gelfix 5 or Adhere 60 from Nitral Urbana Laoboratories,
Brazil, a BASF Company), B. japonicum SEMIA 5080 (e.g. GELFIX 5 or
ADHERE 60 from Nitral Urbana Laoboratories, Brazil, a BASF
Company), B. mojavensis AP-209 (NRRL B-50616), B. solisalsi AP-217
(NRRL B-50617), B. pumilus strain INR-7 (otherwise referred to as
BU-F22 (NRRL B-50153) and BU-F33 (NRRL B-50185)), B. simplex ABU
288 (NRRL B-50340) and B. amyloliquefaciens subsp. plantarum MBI600
(NRRL B-50595) have been mentioned i.a. in US patent appl.
20120149571, U.S. Pat. No. 8,445,255, WO 2012/079073.
Bradyrhizobium japonicum USDA 3 is known from U.S. Pat. No.
7,262,151.
[0570] Jasmonic acid or salts (jasmonates) or derivatives include
without limitation potassium jasmonate, sodium jasmonate, lithium
jasmonate, ammonium jasmonate, dimethylammonium jasmonate,
isopropylammonium jasmonate, diolammonium jasmonate,
diethtriethanolammonium jasmonate, jasmonic acid methyl ester,
jasmonic acid amide, jasmonic acid methylamide, jasmonic
acid-L-amino acid (amide-linked) conjugates (e.g., conjugates with
L-isoleucine, Lvaline, L-leucine, or L-phenylalanine),
12-oxo-phytodienoic acid, coronatine, coronafacoyl-Lserine,
coronafacoyl-L-threonine, methyl esters of
1-oxo-indanoyl-isoleucine, methyl esters of 1-oxo-indanoyl-leucine,
coronalon
(2-[(6-ethyl-1-oxo-indane-4-carbonyl)-amino]-3-methyl-pentanoic
acid methyl ester), linoleic acid or derivatives thereof and
cis-jasmone, or combinations of any of the above.
[0571] Humates are humic and fulvic acids extracted from a form of
lignite coal and clay, known as leonardite. Humic acids are organic
acids that occur in humus and other organically derived materials
such as peat and certain soft coal. They have been shown to
increase fertilizer efficiency in phosphate and micro-nutrient
uptake by plants as well as aiding in the development of plant root
systems.
[0572] According to one embodiment, the microbial pesticides
selected from groups L1), L3) and L5) embrace not only the
isolated, pure cultures of the respective micro-organism as defined
herein, but also its cell-free extract, its suspensions in a whole
broth culture or as a metabolitecontaining supernatant or a
purified metabolite obtained from a whole broth culture of the
microorganism or microorganism strain.
[0573] According to a further embodiment, the microbial pesticides
selected from groups L1), L3 and L5) embraces not only the
isolated, pure cultures of the respective micro-organism as defined
herein, but also a cell-free extract thereof or at least one
metabolite thereof, and/or a mutant of the respective
micro-organism having all the identifying characteristics thereof
and also a cell-free extract or at least one metabolite of the
mutant.
[0574] "Whole broth culture" refers to a liquid culture containing
both cells and media.
[0575] "Supernatant" refers to the liquid broth remaining when
cells grown in broth are removed by centrifugation, filtration,
sedimentation, or other means well known in the art.
[0576] The term "cell-free extract" refers to an extract of the
vegetative cells, spores and/or the whole culture broth of a
microorganism comprising cellular metabolites produced by the
respective microorganism obtainable by cell disruption methods
known in the art such as solvent-based (e.g. organic solvents such
as alcohols sometimesin combination with suitable salts),
temperature-based, application of shear forces, cell disrupotion
with an ultrasonicator. The desired extract may be concentrated by
conventional concentration techniques such as drying, evaporation,
centrifugation or alike. Certain washing steps using organic
solents and/or water-based media may also be applied to the crude
extract preferably prior to use.
[0577] The term "metabolite" refers to any compound, substance or
byproduct produced by a microorganism (such as fungi and bacteria)
that has improves plant growth, water use efficiency of the plant,
plant health, plant appearance, or the population of beneficial
microorganisms in the soil around the plant activity.
[0578] The term "mutant" refers a microorganism obtained by direct
mutant selection but also includes microorganisms that have been
further mutagenized or otherwise manipulated (e.g., via the
introduction of a plasmid). Accordingly, embodiments include
mutants, variants, and or derivatives of the respective
microorganism, both naturally occurring and artificially induced
mutants. For example, mutants may be induced by subjecting the
microorganism to known mutagens, such as N-methyl-nitrosoguanidine,
using conventional methods.
[0579] Suitable bactericides are bronopol and isothiazolinone
derivatives such as alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene
glycol, urea and glycerin. Suitable anti-foaming agents are
silicones, long chain alcohols, and salts of fatty acids. Suitable
colorants (e.g. in red, blue, or green) are pigments of low water
solubility and water-soluble dyes. Examples are inorganic colorants
(e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic
colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidons,
polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or
synthetic waxes, and cellulose ethers.
[0580] In the case of mixtures comprising microbial pesticides II
selected from groups L1), L3) and L5), the microorganisms as used
according to the invention can be cultivated continuously or
discontinuously in the batch process or in the fed batch or
repeated fed batch process. A review of known methods of
cultivation will be found in the textbook by Chmiel
(Bioprozesstechnik 1. Einfuhrung in die Bioverfahrenstechnik
(Gustav Fischer Verlag, Stuttgart, 1991)) or in the textbook by
Storhas (Bioreaktoren and periphere Einrichtungen (Vieweg Verlag,
Braunschweig/Wiesbaden, 1994)).
[0581] When living microorganisms, such as pesticides II from
groups L1), L3) and L5), form part of the compositions, such
compositions can be prepared as compositions comprising besides the
active ingredients at least one auxiliary (inert ingredient) by
usual means (see e.g. H. D. Burges: Formulation of Micobial
Biopestcides, Springer, 1998). Suitable customary types of such
compositions are suspensions, dusts, powders, pastes, granules,
pressings, capsules, and mixtures thereof. Examples for composition
types are suspensions (e.g. SC, OD, FS), capsules (e.g. CS, ZC),
pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP,
DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG,
GG, MG), insecticidal articles (e.g. LN), as well as gel
formulations for the treatment of plant propagation materials such
as seeds (e.g. GF). Herein, it has to be taken into account that
each formulation type or choice of auxiliary should not influence
the viability of the microorganism during storage of thecomposition
and when finally applied to the soil, plant or plant propagation
material. Suitable formulations are e.g. mentioned in WO
2008/002371, U.S. Pat. No. 6,955,912, U.S. Pat. No. 5,422,107.
[0582] Examples for suitable auxiliaries are those mentioned
earlier herein, wherein it must be taken care that choice and
amounts of such auxiliaries should not influence the viability of
the microbial pesticides in the composition. Especially for
bactericides and solvents, compatibility with the respective
microorganism of the respective microbial pesticide has to be taken
into account. In addition, compositions with microbial pesticides
may further contain stabilizers or nutrients and UV protectants.
Suitable stabilzers or nutrients are e.g. alpha-tocopherol,
trehalose, glutamate, potassium sorbate, various sugars like
glucose, sucrose, lactose and maltodextrine (H. D. Burges:
Formulation of Micobial Biopestcides, Springer, 1998). Suitable UV
protectants are e.g. inorganic compouns like titan dioxide, zinc
oxide and iron oxide pigments or organic compounds like
benzophenones, benzotriazoles and phenyltriazines. The compositions
may in addition to auxiliaries mentioned for compositions
comprising compounds I herein optionally comprise 0.1--80%
stabilizers or nutrients and 0.1-10% UV protectants.
[0583] When mixtures comprising microbial pesticides are employed
in crop protection, the application rates preferably range from
about 1.times.10.sup.6 to 5.times.10.sup.15 (or more) CFU/ha.
Preferably, the spore concentration is about 1.times.10.sup.7 to
about 1.times.10.sup.11 CFU/ha. In the case of (entomopathogenic)
nematodes as microbial pesticides (e.g. Steinernema feltiae), the
application rates preferably range inform about 1.times.10.sup.5 to
1.times.10.sup.12 (or more), more preferably from 1.times.10.sup.8
to 1.times.10.sup.11, even more preferably from 5.times.10.sup.8 to
1.times.10.sup.10 individuals (e.g. in the form of eggs, juvenile
or any other live stages, preferably in an infective juvenile
stage) per ha.
[0584] When mixtures comprising microbial pesticides are employed
in seed treatment, the application rates with respect to plant
propagation material preferably range from about 1.times.10.sup.6
to 1.times.10.sup.12 (or more) CFU/seed. Preferably, the
concentration is about 1.times.10.sup.6 to about 1.times.10.sup.11
CFU/seed. In the case of the microbial pesticides II, the
application rates with respect to plant propagation material also
preferably range from about 1.times.10.sup.7 to 1.times.10.sup.14
(or more) CFU per 100 kg of seed, preferably from 1.times.10.sup.9
to about 1.times.10.sup.11 CFU per 100 kg of seed.
[0585] Accordingly, the present invention furthermore relates to
compositions comprising one compound I (component 1) and one
further active substance (component 2), which further active
substance is selected from the column "Component 2" of the lines
C-1 to C-398 of Table C.
[0586] A further embodiment relates to the compositions C-1 to
C-398 listed in Table C, wherein one row of Table C corresponds in
each case to a composition comprising one of the compounds I that
are individualized compounds of formula I (component 1) and the
respective further active substance from groups A) to O) (component
2) stated in the respective row. According to a preferred
embodiment, the "individualized compound I" is one of the compounds
as individualized in Tables 1a to 70a, Tables 1 b to 70b and Tables
1c to 70c or one of the inventive compounds as given in Table I.
Preferably, the compositions described comprise the active
substances in synergistically effective amounts.
TABLE-US-00007 TABLE C Composition comprising one individualized
compound of the present invention and one further active substance
from groups A) to O) composition Component 1 Component 2 C-1 one
individualized compound I Azoxystrobin C-2 one individualized
compound I Coumethoxystrobin C-3 one individualized compound I
Coumoxystrobin C-4 one individualized compound I Dimoxystrobin C-5
one individualized compound I Enestroburin C-6 one individualized
compound I Fenaminstrobin C-7 one individualized compound I
Fenoxystrobin/Flufenoxystrobin C-8 one individualized compound I
Fluoxastrobin C-9 one individualized compound I Kresoxim-methyl
C-10 one individualized compound I Metominostrobin C-11 one
individualized compound I Orysastrobin C-12 one individualized
compound I Picoxystrobin C-13 one individualized compound I
Pyraclostrobin C-14 one individualized compound I Pyrametostrobin
C-15 one individualized compound I Pyraoxystrobin C-16 one
individualized compound I Pyribencarb C-17 one individualized
compound I Trifloxystrobin C-18 one individualized compound I
Triclopyricarb/Chlorodincarb C-19 one individualized compound I
2-[2-(2,5-dimethyl-phenoxymethyl)- phenyl]-3-methoxy-acrylic acid
methyl ester C-20 one individualized compound I
2-(2-(3-(2,6-dichlorophenyl)-1-methyl-
allylideneaminooxymethyl)-phenyl)-
2-methoxyimino-N-methyl-acetamide C-21 one individualized compound
I Benalaxyl C-22 one individualized compound I Benalaxyl-M C-23 one
individualized compound I Benodanil C-24 one individualized
compound I Benzovindiflupyr C-25 one individualized compound I
Bixafen C-26 one individualized compound I Boscalid C-27 one
individualized compound I Carboxin C-28 one individualized compound
I Fenfuram C-29 one individualized compound I Fenhexamid C-30 one
individualized compound I Flutolanil C-31 one individualized
compound I Fluxapyroxad C-32 one individualized compound I
Furametpyr C-33 one individualized compound I Isopyrazam C-34 one
individualized compound I Isotianil C-35 one individualized
compound I Kiralaxyl C-36 one individualized compound I Mepronil
C-37 one individualized compound I Metalaxyl C-38 one
individualized compound I Metalaxyl-M C-39 one individualized
compound I Ofurace C-40 one individualized compound I Oxadixyl C-41
one individualized compound I Oxycarboxin C-42 one individualized
compound I Penflufen C-43 one individualized compound I
Penthiopyrad C-44 one individualized compound I Sedaxane C-45 one
individualized compound I Tecloftalam C-46 one individualized
compound I Thifluzamide C-47 one individualized compound I Tiadinil
C-48 one individualized compound I 2-Amino-4-methyl-thiazole-5-
carboxylic acid anilide C-49 one individualized compound I
N-(4'-trifluoromethylthiobiphenyl-2-yl)-
3-difluoromethyl-1-methyl-1H- pyrazole-4-carboxamide C-50 one
individualized compound I N-(2-(1,3,3-trimethyl-butyl)-phenyl)-
1,3-dimethyl-5-fluoro-1H-pyrazole- 4-carboxamide C-51 one
individualized compound I 3-(difluoromethyl)-1-methyl-N-(1,1,3-
trimethylindan-4-yl)pyrazole-4-carbox- amide C-52 one
individualized compound I 3-(trifluoromethyl)-1-methyl-N-(1,1,3-
trimethylindan-4-yl)pyrazole-4-carbox- amide C-53 one
individualized compound I 1,3-dimethyl-N-(1,1,3-trimethylindan-
4-yl)pyrazole-4-carboxamide C-54 one individualized compound I
3-(trifluoromethyl)-1,5-dimethyl-
N-(1,1,3-trimethylindan-4-yl)pyrazole- 4-carboxamide C-55 one
individualized compound I 3-(difluoromethyl)-1,5-dimethyl-
N-(1,1,3-trimethylindan-4-yl)pyrazole- 4-carboxamide C-56 one
individualized compound I 1,3,5-trimethyl-N-(1,1,3-
trimethylindan-4-yl)pyrazole-4- carboxamide C-57 one individualized
compound I Dimethomorph C-58 one individualized compound I Flumorph
C-59 one individualized compound I Pyrimorph C-60 one
individualized compound I Flumetover C-61 one individualized
compound I Fluopicolide C-62 one individualized compound I
Fluopyram C-63 one individualized compound I Zoxamide C-64 one
individualized compound I Carpropamid C-65 one individualized
compound I Diclocymet C-66 one individualized compound I
Mandipropamid C-67 one individualized compound I Oxytetracyclin
C-68 one individualized compound I Silthiofam C-69 one
individualized compound I N-(6-methoxy-pyridin-3-yl)
cyclopropanecarboxylic acid amide C-70 one individualized compound
I Azaconazole C-71 one individualized compound I Bitertanol C-72
one individualized compound I Bromuconazole C-73 one individualized
compound I Cyproconazole C-74 one individualized compound I
Difenoconazole C-75 one individualized compound I Diniconazole C-76
one individualized compound I Diniconazole-M C-77 one
individualized compound I Epoxiconazole C-78 one individualized
compound I Fenbuconazole C-79 one individualized compound I
Fluquinconazole C-80 one individualized compound I Flusilazole C-81
one individualized compound I Flutriafol C-82 one individualized
compound I Hexaconazol C-83 one individualized compound I
Imibenconazole C-84 one individualized compound I Ipconazole C-85
one individualized compound I Metconazole C-86 one individualized
compound I Myclobutanil C-87 one individualized compound I
Oxpoconazol C-88 one individualized compound I Paclobutrazol C-89
one individualized compound I Penconazole C-90 one individualized
compound I Propiconazole C-91 one individualized compound I
Prothioconazole C-92 one individualized compound I Simeconazole
C-93 one individualized compound I Tebuconazole C-94 one
individualized compound I Tetraconazole C-95 one individualized
compound I Triadimefon C-96 one individualized compound I
Triadimenol C-97 one individualized compound I Triticonazole C-98
one individualized compound I Uniconazole C-99 one individualized
compound I 1-[rel-(2S;3R)-3-(2-chlorophenyl)-
2-(2,4-difluorophenyl)-oxiranylmethyl]-
5-thiocyanato-1H-[1,2,4]triazole, C-100 one individualized compound
I 2-[rel-(2S;3R)-3-(2-chlorophenyl)-
2-(2,4-difluorophenyl)-oxiranylmethyl]- 2H-[1,2,4]triazole-3-thiol
C-101 one individualized compound I Cyazofamid C-102 one
individualized compound I Amisulbrom C-103 one individualized
compound I Imazalil C-104 one individualized compound I
Imazalil-sulfate C-105 one individualized compound I Pefurazoate
C-106 one individualized compound I Prochloraz C-107 one
individualized compound I Triflumizole C-108 one individualized
compound I Benomyl C-109 one individualized compound I Carbendazim
C-110 one individualized compound I Fuberidazole C-111 one
individualized compound I Thiabendazole C-112 one individualized
compound I Ethaboxam C-113 one individualized compound I
Etridiazole C-114 one individualized compound I Hymexazole C-115
one individualized compound I
2-(4-Chloro-phenyl)-N-[4-(3,4-dimethoxy-
phenyl)-isoxazol-5-yl]-2-prop-2- ynyloxy-acetamide C-116 one
individualized compound I Fluazinam C-117 one individualized
compound I Pyrifenox C-118 one individualized compound I
3-[5-(4-Chloro-phenyl)-2,3-dimethyl-is- oxazolidin-3-yl]-pyridine
(Pyrisoxazole) C-119 one individualized compound I
3-[5-(4-Methyl-phenyl)-2,3-dimethyl- isoxazolid in-3-yl]-pyridine
C-120 one individualized compound I Bupirimate C-121 one
individualized compound I Cyprodinil C-122 one individualized
compound I 5-Fluorocytosine C-123 one individualized compound I
5-Fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine C-124 one
individualized compound I 5-Fluoro-2-(4-fluorophenylmethoxy)-
pyrimidin-4-amine C-125 one individualized compound I Diflumetorim
C-126 one individualized compound I
(5,8-Difluoroquinazolin-4-yl)-{2-[2-fluoro-
4-(4-trifluoromethylpyridin-2-yloxy)- phenyl]-ethyl}-amine C-127
one individualized compound I Fenarimol C-128 one individualized
compound I Ferimzone C-129 one individualized compound I
Mepanipyrim C-130 one individualized compound I Nitrapyrin C-131
one individualized compound I Nuarimol C-132 one individualized
compound I Pyrimethanil C-133 one individualized compound I
Triforine C-134 one individualized compound I Fenpiclonil C-135 one
individualized compound I Fludioxonil C-136 one individualized
compound I Aldimorph C-137 one individualized compound I Dodemorph
C-138 one individualized compound I Dodemorph-acetate C-139 one
individualized compound I Fenpropimorph C-140 one individualized
compound I Tridemorph C-141 one individualized compound I
Fenpropidin C-142 one individualized compound I Fluoroimid C-143
one individualized compound I Iprodione C-144 one individualized
compound I Procymidone C-145 one individualized compound I
Vinclozolin C-146 one individualized compound I Famoxadone C-147
one individualized compound I Fenamidone C-148 one individualized
compound I Flutianil C-149 one individualized compound I
Octhilinone C-150 one individualized compound I Probenazole C-151
one individualized compound I Fenpyrazamine C-152 one
individualized compound I Acibenzolar-S-methyl C-153 one
individualized compound I Ametoctradin C-154 one individualized
compound I Amisulbrom C-155 one individualized compound I
[(3S,6S,7R,8R)-8-benzyl-3-[(3- isobutyryloxymethoxy-4-
methoxypyridine-2-carbonyl)amino]-6-
methyl-4,9-dioxo-[1,5]dioxonan-7-yl] 2-methylpropanoate C-156 one
individualized compound I [(3S,6S,7R,8R)-8-benzyl-3-[(3-
acetoxy-4-methoxy-pyridine-2- carbonyl)amino]-6-methyl-4,9-dioxo-
1,5-dioxonan-7-yl] 2-methylpropanoate C-157 one individualized
compound I [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-
4-methoxy-pyridine- 2-carbonyl]amino]-6-methyl-4,9-dioxo-
1,5-dioxonan-7-yl] 2- methylpropanoate C-158 one individualized
compound I [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-
4-methoxy-pyridine- 2-carbonyl)amino]-6-methyl-4,9-dioxo-
1,5-dioxonan-7-yl] 2- methylpropanoate C-159 one individualized
compound I [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-
benzodioxol-5-ylmethoxy)-4-methoxy-
pyridine-2-carbonyl]amino]-6-methyl- 4,9-dioxo-1,5-dioxonan-7-yl]
2-methyl- propanoate C-160 one individualized compound I
(3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-
2-pyridinyl)carbonyl]amino]- 6-methyl-4,9-dioxo-8-(phenylmethyl)-
1,5-dioxonan-7-yl 2-methylpropanoate C-161 one individualized
compound I Anilazin C-162 one individualized compound I
Blasticidin-S C-163 one individualized compound I Captafol C-164
one individualized compound I Captan C-165 one individualized
compound I Chinomethionat C-166 one individualized compound I
Dazomet C-167 one individualized compound I Debacarb C-168 one
individualized compound I Diclomezine C-169 one individualized
compound I Difenzoquat, C-170 one individualized compound I
Difenzoquat-methylsulfate C-171 one individualized compound I
Fenoxanil C-172 one individualized compound I Folpet C-173 one
individualized compound I Oxolinsaure C-174 one individualized
compound I Piperalin C-175 one individualized compound I
Proquinazid C-176 one individualized compound I Pyroquilon C-177
one individualized compound I Quinoxyfen C-178 one individualized
compound I Triazoxid C-179 one individualized compound I
Tricyclazole
C-180 one individualized compound I
2-Butoxy-6-iodo-3-propyl-chromen-4- one C-181 one individualized
compound I 5-Chloro-1-(4,6-dimethoxy-pyrimidin-
2-yl)-2-methyl-1H-benzoimidazole C-182 one individualized compound
I 5-Chloro-7-(4-methyl-piperidin-1-yl)-
6-(2,4,6-trifluoro-phenyl)-[1,2,4]tri- azolo[1,5-a]pyrimidine C-183
one individualized compound I Ferbam C-184 one individualized
compound I Mancozeb C-185 one individualized compound I Maneb C-186
one individualized compound I Metam C-187 one individualized
compound I Methasulphocarb C-188 one individualized compound I
Metiram C-189 one individualized compound I Propineb C-190 one
individualized compound I Thiram C-191 one individualized compound
I Zineb C-192 one individualized compound I Ziram C-193 one
individualized compound I Diethofencarb C-194 one individualized
compound I Benthiavalicarb C-195 one individualized compound I
Iprovalicarb C-196 one individualized compound I Propamocarb C-197
one individualized compound I Propamocarb hydrochlorid C-198 one
individualized compound I Valifenalate C-199 one individualized
compound I N-(1-(1-(4-cyanophenyl)ethanesulfonyl)- but-2-yl)
carbamic acid-(4-fluoro- phenyl) ester C-200 one individualized
compound I Dodine C-201 one individualized compound I Dodine free
base C-202 one individualized compound I Guazatine C-203 one
individualized compound I Guazatine-acetate C-204 one
individualized compound I Iminoctadine C-205 one individualized
compound I Iminoctadine-triacetate C-206 one individualized
compound I Iminoctadine-tris(albesilate) C-207 one individualized
compound I Kasugamycin C-208 one individualized compound I
Kasugamycin-hydrochloride-hydrate C-209 one individualized compound
I Polyoxine C-210 one individualized compound I Streptomycin C-211
one individualized compound I Validamycin A C-212 one
individualized compound I Binapacryl C-213 one individualized
compound I Dicloran C-214 one individualized compound I Dinobuton
C-215 one individualized compound I Dinocap C-216 one
individualized compound I Nitrothal-isopropyl C-217 one
individualized compound I Tecnazen C-218 one individualized
compound I Fentin salts C-219 one individualized compound I
Dithianon C-220 one individualized compound I
2,6-dimethyl-1H,5H-[1,4]dithiino [2,3-c:5,6-c']dipyrrole-
1,3,5,7(2H,6H)-tetraone C-221 one individualized compound I
Isoprothiolane C-222 one individualized compound I Edifenphos C-223
one individualized compound I Fosetyl, Fosetyl-aluminium C-224 one
individualized compound I Iprobenfos C-225 one individualized
compound I Phosphorous acid (H.sub.3PO.sub.3) and derivatives C-226
one individualized compound I Pyrazophos C-227 one individualized
compound I Tolclofos-methyl C-228 one individualized compound I
Chlorothalonil C-229 one individualized compound I Dichlofluanid
C-230 one individualized compound I Dichlorophen C-231 one
individualized compound I Flusulfamide C-232 one individualized
compound I Hexachlorbenzene C-233 one individualized compound I
Pencycuron C-234 one individualized compound I Pentachlorophenol
and salts C-235 one individualized compound I Phthalide C-236 one
individualized compound I Quintozene C-237 one individualized
compound I Thiophanate Methyl C-238 one individualized compound I
Tolylfluanid C-239 one individualized compound I
N-(4-chloro-2-nitro-phenyl)-N-ethyl- 4-methyl-benzenesulfonamide
C-240 one individualized compound I Bordeaux mixture C-241 one
individualized compound I Copper acetate C-242 one individualized
compound I Copper hydroxide C-243 one individualized compound I
Copper oxychloride C-244 one individualized compound I basic Copper
sulfate C-245 one individualized compound I Sulfur C-246 one
individualized compound I Biphenyl C-247 one individualized
compound I Bronopol C-248 one individualized compound I
Cyflufenamid C-249 one individualized compound I Cymoxanil C-250
one individualized compound I Diphenylamin C-251 one individualized
compound I Metrafenone C-252 one individualized compound I
Pyriofenone C-253 one individualized compound I Mildiomycin C-254
one individualized compound I Oxin-copper C-255 one individualized
compound I Oxathiapiprolin C-256 one individualized compound I
Prohexadione calcium C-257 one individualized compound I
Spiroxamine C-258 one individualized compound I Tebufloquin C-259
one individualized compound I Tolylfluanid C-260 one individualized
compound I N-(Cyclopropylmethoxyimino-(6-
difluoromethoxy-2,3-difluoro-phenyl)- methyl)-2-phenyl acetamide
C-261 one individualized compound I
N'-(4-(4-chloro-3-trifluoromethyl- phenoxy)-2,5-dimethyl-phenyl)-N-
ethyl-N-methyl formamidine C-262 one individualized compound I
N'-(4-(4-fluoro-3-trifluoromethyl- phenoxy)-2,5-dimethyl-phenyl)-N-
ethyl-N-methyl formamidine C-263 one individualized compound I
N'-(2-methyl-5-trifluoromethyl-4-(3-tri-
methylsilanyl-propoxy)-phenyl)-N- ethyl-N-methyl formamidine C-264
one individualized compound I
N'-(5-difluoromethyl-2-methyl-4-(3-tri-
methylsilanyl-propoxy)-phenyl)-N- ethyl-N-methyl formamidine C-265
one individualized compound I Methoxy-acetic acid 6-tert-butyl-8-
fluoro-2,3-dimethyl-quinolin-4-yl ester C-266 one individualized
compound I Bacillus subtilis NRRL No. B-21661 C-267 one
individualized compound I Bacillus pumilus NRRL No. B-30087 C-268
one individualized compound I Ulocladium oudemansii C-269 one
individualized compound I Carbaryl C-270 one individualized
compound I Carbofuran C-271 one individualized compound I
Carbosulfan C-272 one individualized compound I Methomylthiodicarb
C-273 one individualized compound I Bifenthrin C-274 one
individualized compound I Cyfluthrin C-275 one individualized
compound I Cypermethrin C-276 one individualized compound I
alpha-Cypermethrin C-277 one individualized compound I
zeta-Cypermethrin C-278 one individualized compound I Deltamethrin
C-279 one individualized compound I Esfenvalerate C-280 one
individualized compound I Lambda-cyhalothrin C-281 one
individualized compound I Permethrin C-282 one individualized
compound I Tefluthrin C-283 one individualized compound I
Diflubenzuron C-284 one individualized compound I Flufenoxuron
C-285 one individualized compound I Lufenuron C-286 one
individualized compound I Teflubenzuron C-287 one individualized
compound I Spirotetramate C-288 one individualized compound I
Clothianidin C-289 one individualized compound I Dinotefuran C-290
one individualized compound I Imidacloprid C-291 one individualized
compound I Thiamethoxam C-292 one individualized compound I
Flupyradifurone C-293 one individualized compound I Acetamiprid
C-294 one individualized compound I Thiacloprid C-295 one
individualized compound I Endosulfan C-296 one individualized
compound I Fipronil C-297 one individualized compound I Abamectin
C-298 one individualized compound I Emamectin C-299 one
individualized compound I Spinosad C-300 one individualized
compound I Spinetoram C-301 one individualized compound I
Hydramethylnon C-302 one individualized compound I Chlorfenapyr
C-303 one individualized compound I Fenbutatin oxide C-304 one
individualized compound I Indoxacarb C-305 one individualized
compound I Metaflumizone C-306 one individualized compound I
Flonicamid C-307 one individualized compound I Lubendiamide C-308
one individualized compound I Chlorantraniliprole C-309 one
individualized compound I Cyazypyr (HGW86) C-310 one individualized
compound I Cyflumetofen C-311 one individualized compound I
Acetochlor C-312 one individualized compound I Dimethenamid C-313
one individualized compound I metolachlor C-314 one individualized
compound I Metazachlor C-315 one individualized compound I
Glyphosate C-316 one individualized compound I Glufosinate C-317
one individualized compound I Sulfosate C-318 one individualized
compound I Clodinafop C-319 one individualized compound I
Fenoxaprop C-320 one individualized compound I Fluazifop C-321 one
individualized compound I Haloxyfop C-322 one individualized
compound I Paraquat C-323 one individualized compound I
Phenmedipham C-324 one individualized compound I Clethodim C-325
one individualized compound I Cycloxydim C-326 one individualized
compound I Profoxydim C-327 one individualized compound I
Sethoxydim C-328 one individualized compound I Tepraloxydim C-329
one individualized compound I Pendimethalin C-330 one
individualized compound I Prodiamine C-331 one individualized
compound I Trifluralin C-332 one individualized compound I
Acifluorfen C-333 one individualized compound I Bromoxynil C-334
one individualized compound I Imazamethabenz C-335 one
individualized compound I Imazamox C-336 one individualized
compound I Imazapic C-337 one individualized compound I Imazapyr
C-338 one individualized compound I Imazaquin C-339 one
individualized compound I Imazethapyr C-340 one individualized
compound I 2,4-Dichlorophenoxyacetic acid (2,4- D) C-341 one
individualized compound I Chloridazon C-342 one individualized
compound I Clopyralid C-343 one individualized compound I
Fluroxypyr C-344 one individualized compound I Picloram C-345 one
individualized compound I Picolinafen C-346 one individualized
compound I Bensulfuron C-347 one individualized compound I
Chlorimuron-ethyl C-348 one individualized compound I
Cyclosulfamuron C-349 one individualized compound I Iodosulfuron
C-350 one individualized compound I Mesosulfuron C-351 one
individualized compound I Metsulfuron-methyl C-352 one
individualized compound I Nicosulfuron C-353 one individualized
compound I Rimsulfuron C-354 one individualized compound I
Triflusulfuron C-355 one individualized compound I Atrazine C-356
one individualized compound I Hexazinone C-357 one individualized
compound I Diuron C-358 one individualized compound I Florasulam
C-359 one individualized compound I Pyroxasulfone C-360 one
individualized compound I Bentazone C-361 one individualized
compound I Cinidon-ethyl C-362 one individualized compound I
Cinmethylin C-363 one individualized compound I Dicamba C-364 one
individualized compound I Diflufenzopyr C-365 one individualized
compound I Quinclorac C-366 one individualized compound I Quinmerac
C-367 one individualized compound I Mesotrione C-368 one
individualized compound I Saflufenacil C-369 one individualized
compound I Topramezone C-370 one individualized compound I
1,1'-[(3S,4R,4aR,6S,6aS,12R,12aS, 12bS)-4-[[(2-
cyclopropylacetyl)oxy]methyl]- 1,3,4,4a,5,6,6a,12,12a,12b-deca-
hydro-12-hydroxy-4,6a,12b-trimethyl-
11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,
1-b]pyrano[3,4-e]pyran-3,6-diyl] cyclopropaneacetic acid ester
C-371 one individualized compound I (3S,6S,7R,8R)-3-[[(3-hydroxy-4-
methoxy-2-pyridinyl)carbonyl]amino]-
6-methyl-4,9-dioxo-8-(phenylmethyl)- 1,5-dioxonan-7-yl
2-methylpropanoate C-372 one individualized compound I isofetamid
C-373 one individualized compound I
N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-
1,3-dimethyl-pyrazole-4-carboxamide C-374 one individualized
compound I N-[2-(2,4-dichlorophenyl)-2-methoxy-
1-methyl-ethyl]-3-(difluoromethyl)-1- methyl-pyrazole-4-carboxamide
C-375 one individualized compound I
2-[2-chloro-4-(4-chlorophenoxy)-
phenyl]-1-(1,2,4-triazol-1-yl)pentan-2- ol C-376 one individualized
compound I 1-[4-(4-chlorophenoxy)-2-(trifluoro-
methyl)phenyl]-1-cyclopropyl-2-(1,2,4- triazol-1-yl)ethanol C-377
one individualized compound I 2-[4-(4-chlorophenoxy)-2-
(trifluoromethyl)phenyl]-1-(1,2,4- triazol-1-yl)butan-2-ol C-378
one individualized compound I 2-[2-chloro-4-(4-
chlorophenoxy)phenyl]-1-(1,2,4- triazol-1-yl)butan-2-ol C-379 one
individualized compound I 2-[4-(4-chlorophenoxy)-2-
(trifluoromethyl)phenyl]-3-methyl-1- (1,2,4-triazol-1-yl)butan-2-ol
C-380 one individualized compound I 2-[4-(4-chlorophenoxy)-2-
(trifluoromethyl)phenyl]-1-(1,2,4-
triazol-1-yl)propan-2-ol C-381 one individualized compound I
2-[2-chloro-4-(4- chlorophenoxy)phenyl]-3-methyl-1-
(1,2,4-triazol-1-yl)butan-2-ol C-382 one individualized compound I
2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-1-(1,2,4-
triazol-1-yl)pentan-2-ol C-383 one individualized compound I
2-[4-(4-fluorophenoxy)-2- (trifluoromethyl)phenyl]-1-(1,2,4-
triazol-1-yl)propan-2-ol C-384 one individualized compound I
3-(4-chloro-2-fluoro-phenyl)-5-(2,4-
difluorophenyl)isoxazol-4-yl]-(3- pyridyl)methanol C-385 one
individualized compound I 2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-
pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-
thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5- yl}phenyl methanesulfonate
C-386 one individualized compound I
2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-
pyrazol-1-yl]acetyl}piperidin-4-yl) 1,3-
thiazol-4-yl]-4,5-dihydro-1,2-oxazol- 5-yl}-3-chlorophenyl
methanesulfonate C-387 one individualized compound I tolprocarb
C-388 one individualized compound I
2-[3,5-bis(difluoromethyl)-1H-pyrazol-
1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-
yloxy)phenyl]-4,5-dihydro-1,2-oxazol-
3-yl}-1,3-thiazol-2-yl)piperidin-1- yl]ethanone C-389 one
individualized compound I 2-[3,5-bis(difluoromethyl)-1H-pyrazol-
1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-
1-yloxy)phenyl]-4,5-dihydro-1,2-
oxazol-3-yl}-1,3-thiazol-2-yl)piperidin- 1-yl]ethanone C-390 one
individualized compound I 2-[3,5-bis(difluoromethyl)-1H-pyrazol-
1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-
1-yloxy)phenyl]-4,5-dihydro-1,2-
oxazol-3-yl}-1,3-thiazol-2-yl)piperidin- 1-yl]ethanone C-391 one
individualized compound I ethyl (Z)-3-amino-2-cyano-3-phenyl-
prop-2-enoate, C-392 one individualized compound I picarbutrazox
C-393 one individualized compound I pentyl
N-[6-[[(Z)-[(1-methyltetrazol-5- yl)-phenyl-methylene]amino]oxy-
methyl]-2-pyridyl]carbamate, C-394 one individualized compound I
2-[2-[(7,8-difluoro-2-methyl-3-
quinolyl)oxy]-6-fluoro-phenyl]propan- 2-ol C-395 one individualized
compound I 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-
quinolyl)oxy]phen-yl]propan-2-ol, C-396 one individualized compound
I 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-
dihydroisoquinolin-1-yl)quinoline C-397 one individualized compound
I 3-(4,4-difluoro-3,3-dimethyl-3,4-
dihydroisoquinolin-1-yl)quinoline C-398 one individualized compound
I 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-
dihydroisoquinolin-1-yl)quinoline;
[0587] The active substances referred to as component 2, their
preparation and their activity e.g. against harmful fungi is known
(cf.: http://www.alanwood.net/pesticides/); these substances are
commercially available. The compounds described by IUPAC
nomenclature, their preparation and their fungicidal activity are
also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141
317; EP-A 152 031; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A
428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201
648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE
102005009458; U.S. Pat. No. 3,296,272; U.S. Pat. No. 3,325,503; WO
98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO
00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO
02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO
03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO
04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO
05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO
07/82098; WO 07/90624, WO 11/028657, WO2012/168188, WO 2007/006670,
WO 2011/77514; WO13/047749, WO 10/069882, WO 13/047441, WO
03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO
13/024009 and WO 13/024010).
[0588] The composition of active substances can be prepared as
compositions comprising besides the active ingredients at least one
inert ingredient (auxiliary) by usual means, e.g. by the means
given for the compositions of compounds I.
[0589] Concerning usual ingredients of such compositions reference
is made to the explanations given for the compositions containing
compounds I.
[0590] The compositions of active substances according to the
present invention are suitable as fungicides, as are the compounds
of formula I. They are distinguished by an outstanding
effectiveness against a broad spectrum of phytopathogenic fungi,
especially from the classes of the Ascomycetes, Basidiomycetes,
Deuteromycetes and Peronosporomycetes (syn. Oomycetes). In
addition, it is refered to the explanations regarding the
fungicidal activity of the compounds andthe compositions containing
compounds I, respectively. I. Synthesis examples:
EXAMPLE 1
Synthesis of
2-[2-chloro-4-(2-methylphenoxyl)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-
-ol (Compound I-14, Table I)
Step 1a) Synthesis of
1-(4-bromo-2-chloro-phenyl)-2-chloro-ethanone
[0591] To a mixture 2-Chloro-4-Bromo acetophenone (500 g), MeOH
(137 g) in CH.sub.2Cl.sub.2 (4 L), SO.sub.2Cl.sub.2 (578 g in 1 L
of CH.sub.2Cl.sub.2) was added dropwise, maintaining the
temperature below 30.degree. C. After gas evultion stopped, HPLC
indicated full conversion. H.sub.2O (3 L) was added carefully and
the pH was adjusted to 6.5 using 50% NaOH. The phases were
separated and the aqueous phase extracted with CH.sub.2Cl.sub.2
(2*1 L). The combined organic phases were washed with brine and
dried with Na.sub.2SO.sub.4. The crude compound was obtained as a
viscous oil (608 g) and was used without further purification.
HPLC*: RT=3.096 min; .sup.1H-NMR (300 MHz, CDCI3): .delta.=4.65
(2H), 7.40-7.65 (3H).
Step 1 b) Synthesis of
2-(4-bromo-2-chloro-phenyl)-1-chloro-pent-3-yn-2-ol
[0592] A solution of 1-(4-bromo-2-chloro-phenyl)-2-chloro-ethanone
(267 g in 500 mL CH.sub.2Cl.sub.2) was added dropwise to
prop-1-inyl magnesium bromide (1915 mL of a 0.5M. solution in THF)
at -20.degree. C. and warmed to RT. The reaction mixture was added
to sat. aqu. NH.sub.4CI-solution (5 L) and extracted with
CH.sub.2Cl.sub.2 (3*2 L). the combined organic phases were washd
with brine and dried with Na.sub.2SO.sub.4 and evaporated. The
crude product was used in the next reaction without any further
purification. HPLC*: RT=3.271 min; .sup.1H-NMR (300 MHz, CDCI3):
.delta.=1.85 (3H), 3.95 (1H), 4.20 (1H), 7.45 (1H), 7.55 (1H), 7.80
(1H).
Step 1c) Synthesis of
2-(4-bromo-2-chloro-phenyl)-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol
[0593] 2-(4-bromo-2-chloro-phenyl)-1-chloro-pent-3-yn-2-ol (305 g),
1,2,4-triazole (191 g) and NaOH (83.2 g) were stirred in NMP (2 L)
at 100.degree. C. for 30 min. HPLC indicated full conversion. The
reaction mixture was diluted with sat aqu NH.sub.4Cl (2 L) and
extracted with MTBE (4*2 L) washed with brine (1 L) and dried with
Na.sub.2SO.sub.4. After evaporation, crystallization from
iPr.sub.2O enabled the target compound as colorless crystals (322.6
g). HPLC*: RT=2.629 min; .sup.1H-NMR (300 MHz, CDCI3): 5=1.80 (3H),
4.70 (1H), 4.90 (1H), 7.40 (1H), 7.60 (1H), 7.75 (1H), 7.90 (1H),
8.10 (1H).
Step 1d) Synthesis of
2-[2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-(1,2-
,4-triazol-1-yl)pent-3-yn-2-ol
[0594] A mixture of
2-(4-bromo-2-chloro-phenyl)-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol
(22 g), bis(pinacolato)-diboron (19.2 g) KOAc (5.7 g) abd
PdCl.sub.2dppf (470 mg) in dioxane (200 mL) was heated to
100.degree. C. for 5 h. HPLC indicated full conversion. The
reaction mixture was added to brine (200 mL) and extracted with
EtOAc (3*300 mL). the combined organic phases were dried with
Na.sub.2SO.sub.4 and filtered over a plug of celite. The crude
compound (43 g) was used in the next step without further
purification. HPLC-MS*: RT=1.099 [M=389.8, [M+H.sup.+]]
Step 1e) Synthesis of
3-chloro-4-[1-hydroxy-1-(1,2,4-triazol-1-ylmethyl)but-2-ynyl]phenol
[0595] Crude
2-[2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-(1,2-
,4-triazol-1-yl)pent-3-yn-2-ol (46 g) was dissolved in MeOH (10 mL)
and NaOH (5.7 g) was added. H2O2 (37%, 8.1 mL) was added dropwise.
The mixture was heated to 100.degree. C. and stirred for 30 min.
Water (10 mL) was added and after extraction of the basic aqueous
phase with MTBE (3*30 mL) the aqueous phase was neutralized and
extracted with EtOAc (7*20 mL). the combined Ethyl acetate phases
were dried with Na.sub.2SO.sub.4 and evaporated. The target
compound (10.1 g) was obtained as colorless solid. HPLC-MS*:
RT=0.700 [M=278, [M+H.sup.+]]
Step 1f) Synthesis of
2-[2-chloro-4-(2-methylphenoxyl)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-
-ol
[0596] A mixture of
3-chloro-4-[1-hydroxy-1-(1,2,4-triazol-1-ylmethyl)but-2-ynyl]phenol
(300 mg), 2-Methyl phenyl boronic acid (264 mg), Cu(OAc).sub.2,
NEt.sub.3 (0.5 g), sieves (MS 4A, 1 g) in CH.sub.2Cl.sub.2 (5 mL)
and MeCN (1 mL) were stirred at RT for 14 h. Addition of sat. aqu.
NH.sub.4Cl (10 mL) and extraction with EtOAc (3*15 mL) gave the
crude product and was purified by means of HPLC. To obtain the
clean compound as solid (49 mg); HPLC-MS*: RT=1.151 [M=368,
[M.sup.+]]; .sup.1H-NMR (300 MHz, CDCI3): .delta.=1.80 (3H), 2.20
(3H), 4.75 (1H), 4.90 (1H), 6.75 (1H), 6.95 (2H), 7.10-7.30 (1H),
7.40 (1H), 7.70 (1H), 7.75 (1H), 7.95 (1H), 8.35 (1H).
[0597] The compounds I listed in Table I have been prepared in an
analogous manner.
##STR00025##
TABLE-US-00008 TABLE I compound HPLC * R.sub.t .sup.1H NMR (300
MHz, CDCl.sub.3): No. R.sup.31 (R.sup.4).sub.m R.sup.1 R.sup.2
(min) .delta. (ppm) = I-1 Cl 4-CF.sub.3 CH.sub.3 H 1.183 I-2 Cl
3-CF.sub.3 CH.sub.3 H 1.178 I-3 Cl 3,4-F.sub.2 CH.sub.3 H 1.008 I-4
Cl 2-F CH.sub.3 H 1.070 I-5 Cl 4-CF.sub.3 cyclopropyl H 1.272 I-6
Cl 3-CF.sub.3 cyclopropyl H 1.268 I-7 Cl 4-CN cyclopropyl H 1.115
I-8 Cl 3,5-Cl.sub.2 cyclopropyl H 1.344 I-9 Cl 3-Cl cyclopropyl H
1.247 I-10 Cl 3,4,5-F.sub.3 cyclopropyl H 1.241 I-11 Cl 4-CF.sub.3
C.ident.C--CH.sub.3 H 1.197 I-12 Cl 3,4-Cl.sub.2
C.ident.C--CH.sub.3 H 1.236 I-13 Cl 4-OCF.sub.3 C.ident.C--CH.sub.3
H 1.214 I-14 Cl 2-CH.sub.3 C.ident.C--CH.sub.3 H 1.151 1.80 (3H),
2.20 (3H), 4.75 (1H), 4.90 (1H), 6.75 (1H), 6.95 (2H), 7.10-7.30
(1H), 7.40 (1H), 7.70 (1H), 7.75 (1H), 7.95 (1H), 8.35 (1H). I-15 F
3,4-Cl.sub.2 CH.sub.3 H 1.156 I-16 F 3-Cl CH.sub.3 H 1.082 I-17 F
3,4-F.sub.2 CH.sub.3 H 1.040 I-18 F 3-F CH.sub.3 H 1.026 I-19 F
2-Cl CH.sub.3 H 1.070 I-20** Cl 2-F-4-Cl C.ident.C--CH.sub.3 H
1.132 **not subject mater of the invention *: HPLC method Data:
Mobile Phase: A: Wasser + 0.1% T FA; B: acetonitrile; Gradient: 5%
B to 100% B in 1.5 min; Temperature: 60.degree. C.; MS-Method: ESI
positive; mass area (m/z): 100-700; Flow: 0.8 ml/min to 1.0 ml/min
in 1.5 min; Column: Kinetex XB C18 1.7.mu. 50 .times. 2.1 mm;
Aparatus: Shimadzu Nexera LC-30 LCMS-2020.
* * * * *
References